Microbiocidal heterobicyclic derivatives

ABSTRACT

Compounds of the formula (I) wherein the substituents are as defined in claim  1 . Furthermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or controlling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi.

RELATED APPLICATION INFORMATION

This application is a 371 of International Application No.PCT/EP2016/056127, filed 21 Mar. 2016, which claims priority to EPPatent Application No. 15 16 1494.8, filed 27 Mar. 2015, the contents ofwhich are incorporated herein by reference herein.

The present invention relates to microbiocidal heterobicyclicderivatives, e.g. as active ingredients, which have microbiocidalactivity, in particular fungicidal activity. The invention also relatesto preparation of these heterobicyclic derivatives, to intermediatesuseful in the preparation of these heterobicyclic derivatives, to thepreparation of these intermediates, to agrochemical compositions whichcomprise at least one of the heterobicyclic derivatives, to preparationof these compositions and to the use of the heterobicyclic derivativesor compositions in agriculture or horticulture for controlling orpreventing infestation of plants, harvested food crops, seeds ornon-living materials by phytopathogenic microorganisms, in particularfungi.

Certain fungicidal heterobicyclic compounds are described in WO05070917.

It has now surprisingly been found that certain novel heterobicyclicderivatives have favourable fungicidal properties.

The present invention therefore provides compounds of formula I

wherein

R₁ and R₂ are each independently selected from hydrogen, cyano, C₁-C₆alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl and C₂-C₆ alkynyl, in which thealkyl, cycloalkyl, alkenyl and alkynyl groups may be optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio; or

R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₁₀ cycloalkyl group (which may be optionally substitutedwith 1 to 3 substituents independently selected from the groupconsisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio);

R₃ and R₄ are each independently selected from hydrogen, halogen,hydroxyl, C₁-C₆ alkyl, C₁-C₆ alkoxy, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl andC₂-C₆ alkynyl, in which the alkyl, alkoxy, cycloalkyl, alkenyl andalkynyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio;or

R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a), C═C(R_(b))(R_(c)) or C₃-C₁₀ cycloalkyl (whichmay be optionally substituted with 1 to 3 substituents independentlyselected from the group consisting of a halogen, C₁-C₆ alkyl, C₁-C₆alkoxy and C₁-C₆ alkylthio); or

R₂ and R₃ together with the carbon atoms to which they are attachedrepresent a C₅-C₁₀ cycloalkyl (which may be optionally substituted with1 to 3 substituents independently selected from the group consisting ofhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio, and,additionally, a ring carbon unit may be replaced by an oxygen or sulphuratom);

each R₅ independently represents halogen, hydroxyl, mercapto, nitro,cyano, formyl, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₇cycloalkyl, C₁-C₆ alkoxy, C₃-C₆ alkenyloxy, C₃-C₆ alkynyloxy, C₁-C₆alkylthio, —C(═NOR_(a))C₁-C₆alkyl, C₁-C₆ alkylcarbonyl, aryl,heteroraryl, aryloxy or heteroraryloxy, in which the alkyl, cycloalkyl,alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl and heteroarylgroups may be optionally substituted with 1 to 5 substituentsindependently selected from halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy, cyanoand C₁-C₆ alkylthio; n is 0, 1, 2, 3 or 4;

R₆ is hydrogen, halogen, C₁-C₆ alkyl or C₁-C₆ alkoxy;

each R₇ independently represents hydroxyl, mercapto, cyano, halogen,C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₆haloalkenyl, C₃-C₆ haloalkynyl, C₁-C₆ alkylthio, C₁-C₆ haloalkoxy, C₁-C₆haloalkylthio, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbonyl, C₃-C₇cycloalkyl, C₁-C₆ alkoxy, C₃-C₆ alkenyloxy or C₃-C₆ alkynyloxy; m is 0,1, 2, 3 or 4; or

Two adjacent R₇ substitutents together with the carbon atoms to whichthey are attached represent a C₅-C₇ cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆alkylthio, and, additionally, a ring carbon unit may be replaced by anoxygen or sulphur atom);

R_(a) is selected from hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₃-C₆alkenyl and C₃-C₆ alkynyl, in which the alkyl, cycloalkyl, alkenyl andalkynyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio;

R_(b) and R_(c) are each independently selected from hydrogen, halogen,cyano, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₁-C₆ alkoxy and C₁-C₆ alkylthio, in which the alkyl, cycloalkyl,alkenyl and alkynyl groups may be optionally substituted with 1 to 3substituents independently selected from halogen, C₁-C₆ alkoxy and C₁-C₆alkylthio; or a salt or N-oxide thereof.

In a second aspect the present invention provides an agrochemicalcomposition comprising a compound of formula (I).

Compounds of formula (I) may be used to control phytopathogenicmicroorganisms. Thus, in order to control a phytopathogen a compound offormula (I), or a composition comprising a compound of formula (I),according to the invention may be applied directly to the phytopathogen,or to the locus of a phytopathogen, in particular to a plant susceptibleto attack by phytopathogens.

Thus, in a third aspect the present invention provides the use of acompound of formula (I), or a composition comprising a compound offormula (I), as described herein to control a phytopathogen.

In a further aspect the present invention provides a method ofcontrolling phytopathogens, comprising applying a compound of formula(I), or a composition comprising a compound of formula (I), as describedherein to said phytopathogen, or to the locus of said phytopathogen, inparticular to a plant susceptible to attack by a phytopathogen.

Compounds of formula (I) are particularly effective in the control ofphytopathogenic fungi.

Thus, in a yet further aspect the present invention provides the use ofa compound of formula (I), or a composition comprising a compound offormula (I), as described herein to control phytopathogenic fungi.

In a further aspect the present invention provides a method ofcontrolling phytopathogenic fungi, comprising applying a compound offormula (I), or a composition comprising a compound of formula (I), asdescribed herein to said phytopathogenic fungi, or to the locus of saidphytopathogenic fungi, in particular to a plant susceptible to attack byphytopathogenic fungi.

Where substituents are indicated as being optionally substituted, thismeans that they may or may not carry one or more identical or differentsubstituents, e.g. one to three substituents. Normally not more thanthree such optional substituents are present at the same time. Where agroup is indicated as being substituted, e.g. alkyl, this includes thosegroups that are part of other groups, e.g. the alkyl in alkylthio.

The term “halogen” refers to fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine.

Alkyl substituents may be straight-chained or branched. Alkyl on its ownor as part of another substituent is, depending upon the number ofcarbon atoms mentioned, for example, methyl, ethyl, n-propyl, n-butyl,n-pentyl, n-hexyl and the isomers thereof, for example, iso-propyl,iso-butyl, sec-butyl, tert-butyl or iso-amyl.

Alkenyl substituents can be in the form of straight or branched chains,and the alkenyl moieties, where appropriate, can be of either the (E)-or (Z)-configuration. Examples are vinyl and allyl. The alkenyl groupsare preferably C₂-C₆, more preferably C₂-C₄ and most preferably C₂-C₃alkenyl groups.

Alkynyl substituents can be in the form of straight or branched chains.Examples are ethynyl and propargyl. The alkynyl groups are preferablyC₂-C₆, more preferably C₂-C₄ and most preferably C₂-C₃ alkynyl groups.

Haloalkyl groups may contain one or more identical or different halogenatoms and, for example, may stand for CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂,CF₃, CF₃CH₂, CH₃CF₂, CF₃CF₂ or CCl₃CCl₂.

Haloalkenyl groups are alkenyl groups, respectively, which aresubstituted with one or more of the same or different halogen atoms andare, for example, 2,2-difluorovinyl or 1,2-dichloro-2-fluoro-vinyl.

Haloalkynyl groups are alkynyl groups, respectively, which aresubstituted with one or more of the same or different halogen atoms andare, for example, 1-chloro-prop-2-ynyl.

Alkoxy means a radical —OR, where R is alkyl, e.g. as defined above.Alkoxy groups include, but are not limited to, methoxy, ethoxy,1-methylethoxy, propoxy, butoxy, 1-methylpropoxy and 2-methylpropoxy.

Cyano means a —CN group.

Amino means an —NH₂ group.

Hydroxyl or hydroxy stands for a —OH group.

Aryl groups (either alone or as part of a larger group, such as e.g.aryloxy, aryl-alkyl) are aromatic ring systems which can be in mono-,bi- or tricyclic form. Examples of such rings include phenyl, naphthyl,anthracenyl, indenyl or phenanthrenyl. Preferred aryl groups are phenyland naphthyl, phenyl being most preferred. Where an aryl moiety is saidto be substituted, the aryl moiety is preferably substituted by one tofour substituents, most preferably by one to three substituents.

Heteroaryl groups (either alone or as part of a larger group, such ase.g. heteroaryloxy, heteroaryl-alkyl) are aromatic ring systemscontaining at least one heteroatom and consisting either of a singlering or of two or more fused rings. Preferably, single rings willcontain up to three heteroatoms and bicyclic systems up to fourheteroatoms which will preferably be chosen from nitrogen, oxygen andsulfur. Examples of monocyclic groups include pyridyl, pyridazinyl,pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g.[1,2,4] triazolyl), furanyl, thiophenyl, oxazolyl, isoxazolyl,oxadiazolyl, thiazolyl, isothiazolyl and thiadiazolyl. Examples ofbicyclic groups include purinyl, quinolinyl, cinnolinyl, quinoxalinyl,indolyl, indazolyl, benzimidazolyl, benzothiophenyl and benzothiazolyl.Monocyclic heteroaryl groups are preferred, pyridyl being mostpreferred. Where a heteroaryl moiety is said to be substituted, theheteroaryl moiety is preferably substituted by one to four substituents,most preferably by one to three substituents.

Heterocyclyl groups or heterocyclic rings (either alone or as part of alarger group, such as heterocyclyl-alkyl) are non-aromatic ringstructures containing up to 10 atoms including one or more (preferablyone, two or three) heteroatoms selected from O, S and N. Examples ofmonocyclic groups include, oxetanyl, 4,5-dihydro-isoxazolyl, thietanyl,pyrrolidinyl, tetrahydrofuranyl, [1,3]dioxolanyl, piperidinyl,piperazinyl, [1,4]dioxanyl, imidazolidinyl, [1,3,5]oxadiazinanyl,hexahydro-pyrimidinyl, [1,3,5]triazinanyl and morpholinyl or theiroxidised versions such as 1-oxo-thietanyl and 1,1-dioxo-thietanyl.Examples of bicyclic groups include 2,3-dihydro-benzofuranyl,benzo[1,4]dioxolanyl, benzo[1,3]dioxolanyl, chromenyl, and2,3-dihydro-benzo[1,4]dioxinyl. Where a heterocyclyl moiety is said tobe substituted, the heterocyclyl moiety is preferably substituted by oneto four substituents, most preferably by one to three substituents.

The presence of one or more possible asymmetric carbon atoms in acompound of formula I means that the compounds may occur in opticallyisomeric forms, i.e. enantiomeric or diastereomeric forms. Alsoatropisomers may occur as a result of restricted rotation about a singlebond. Formula I is intended to include all those possible isomeric formsand mixtures thereof. The present invention includes all those possibleisomeric forms and mixtures thereof for a compound of formula I.Likewise, formula I is intended to include all possible tautomers. Thepresent invention includes all possible tautomeric forms for a compoundof formula I.

In each case, the compounds of formula I according to the invention arein free form, in oxidized form as a N-oxide or in salt form, e.g. anagronomically usable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton 1991. It is preferred that the compounds offormula I according to the invention are in free form.

Preferred values of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, Ra, Rb, Rc, n and mare, in any combination thereof, as set out below:

Preferably R₁ and R₂ are each independently selected from hydrogen,C₁-C₆ alkyl and C₃-C₇ cycloalkyl, in which the alkyl and cycloalkylgroups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio;or R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₆ cycloalkyl group (which may be optionally substitutedwith 1 to 3 substituents independently selected from the groupconsisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio).

More preferably R₁ and R₂ are each independently selected from hydrogenand C₁-C₄ alkyl, in which the alkyl group may be optionally substitutedwith 1 to 3 substituents independently selected from halogen, C₁-C₃alkoxy and C₁-C₃ alkylthio; or R₁ and R₂ together with the carbon atomto which they are attached represent a C₃-C₆ cycloalkyl group (which maybe optionally substituted with 1 to 3 substituents independentlyselected from the group consisting of halogen, C₁-C₃ alkyl, C₁-C₃ alkoxyand C₁-C₃ alkylthio).

Even more preferably R₁ and R₂ are each independently selected fromhydrogen and C₁-C₄ alkyl, in which the alkyl group may be optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, methoxy and methylthio; or R₁ and R₂ together with the carbonatom to which they are attached represent a C₃-C₄ cycloalkyl group(which may be optionally substituted with 1 to 3 substituentsindependently selected from the group consisting of halogen and C₁-C₃alkyl).

More preferably still R₁ and R₂ are each independently selected fromhydrogen and C₁-C₃ alkyl; or R₁ and R₂ together with the carbon atom towhich they are attached represent a C₃-C₄ cycloalkyl group.

Most preferably R₁ and R₂ are each independently selected from hydrogenand C₁-C₃ alkyl; or R₁ and R₂ together with the carbon atom to whichthey are attached represent a C₃-C₄ cycloalkyl group.

Preferably R₃ and R₄ are each independently selected from hydrogen,halogen, hydroxyl, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₃-C₇ cycloalkyl, inwhich the alkyl, alkoxy and cycloalkyl groups may be optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio; or R₃ and R₄ together withthe carbon atom to which they are attached represent C═O, C═NOR_(a),C═C(R_(b))(R_(c)) or C₃-C₆ cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of a halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆alkylthio); or R₂ and R₃ together with the carbon atoms to which theyare attached represent a C₅-C₇ cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆alkylthio, and, additionally, a ring carbon unit may be replaced by anoxygen or sulphur atom).

More preferably R₃ and R₄ are each independently selected from hydrogen,halogen, C₁-C₄ alkyl and C₃-C₄ cycloalkyl, in which the alkyl andcycloalkyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₃ alkoxy and C₁-C₃ alkylthio;or R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a), or C₃-C₆ cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of a halogen, C₁-C₃ alkyl, C_(r) C₃ alkoxy and C₁-C₃alkylthio).

Even more preferably R₃ and R₄ are each independently selected fromhydrogen, halogen and C₁-C₄ alkyl, in which the alkyl group may beoptionally substituted with 1 to 3 substituents independently selectedfrom halogen, methoxy and methylthio; or R₃ and R₄ together with thecarbon atom to which they are attached represent C═O, C═NOR_(a) or C₃-C₄cycloalkyl (which may be optionally substituted with 1 to 3 substituentsindependently selected from the group consisting of a halogen and C₁-C₃alkyl).

More preferably still R₃ and R₄ are each independently selected fromhydrogen, halogen and C₁-C₃ alkyl; or R₃ and R₄ together with the carbonatom to which they are attached represent C═O, C═NOR_(a) or C₃-C₄cycloalkyl.

Most preferably R₃ and R₄ are each independently selected from hydrogen,fluoro or C₁-C₃ alkyl; or R₃ and R₄ together with the carbon atom towhich they are attached represent C═O or C₃-C₄ cycloalkyl.

Preferably each R₅ independently represents halogen, cyano, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆alkenyloxy, C₃-C₆ alkynyloxy, C₁-C₆ alkylthio, —C(═NOR_(a))C₁-C₆alkyl,phenyl, heteroraryl (wherein heteroaryl is pyridyl, thiophenyl,thiazolyl, imidazolyl or oxazolyl), phenoxy or heteroraryloxy (whereinheteroaryl is pyridyl, thiophenyl, thiazolyl, imidazolyl or oxazolyl),in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, phenyl and heteroaryl groups may be optionally substitutedwith 1 to 5 substituents independently selected from halogen, C₁-C₆alkyl, C₁-C₆ alkoxy, cyano and C₁-C₆ alkylthio; n is 0, 1, 2, 3 or 4.

More preferably each R₅ independently represents halogen, cyano, C₁-C₄alkyl, C₃-C₄ cycloalkyl, C₁-C₃ alkoxy, C₃-C₆ alkenyloxy, C₃-C₆alkynyloxy, C₁-C₃ alkylthio, —C(═NOR_(a))C₁-C₆alkyl, phenyl, heteroraryl(wherein heteroaryl is pyridyl, thiazolyl or oxazolyl), in which thealkyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, phenyl and heteroarylgroups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₃ alkyl and C₁-C₃ alkoxy; n is0, 1 or 2.

Even more preferably each R₅ independently represents halogen, cyano,C₁-C₄ alkyl, C₃-C₄ cycloalkyl or phenyl, in which the alkyl, cycloalkyland phenyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen or C₁-C₃ alkyl; n is 0, 1 or 2.

More preferably still each R₅ independently represents halogen, cyano,C₁-C₃ alkyl, C₃-C₄ cycloalkyl or phenyl, in which the alkyl, cycloalkyland phenyl groups may be optionally substituted with 1 to 3 halogenatoms; n is 0, 1 or 2.

Most preferably each R₅ independently represents halogen, C₁-C₃ alkyl orC₃-C₄ cycloalkyl, in which the alkyl and cycloalkyl groups may beoptionally substituted with 1 to 3 fluoro atoms; n is 0, 1 or 2.

Preferably R₆ is hydrogen, halogen or C₁-C₆ alkyl.

More preferably R₆ is hydrogen or C₁-C₃ alkyl.

Even more preferably R₆ is hydrogen or methyl.

Most preferably R₆ is hydrogen.

Preferably each R₇ independently represents cyano, halogen, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkenyl, C₃-C₆haloalkynyl, C₁-C₆ alkylthio, C₁-C₆ haloalkoxy, C₁-C₆ haloalkylthio,C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆alkenyloxy or C₃-C₆ alkynyloxy; mis 0, 1, 2, 3 or 4; or

Two adjacent R₇ substituents together with the carbon atoms to whichthey are attached represent a C₅-C₇ cycloalkyl group (which may beoptionally substituted with 1 to 3 substituents independently selectedfrom the group consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy andC₁-C₆ alkylthio, and, additionally, a ring carbon unit may be replacedby an oxygen or sulphur atom).

More preferably each R₇ independently represents cyano, halogen, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkynyl, C₁-C₆ alkylthio, C₁-C₆haloalkoxy, C₁-C₆ haloalkylthio, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆alkenyloxy or C₃-C₆ alkynyloxy; m is 0, 1, 2 or 3; or

Two adjacent R₇ substituents together with the carbon atoms to whichthey are attached represent a C₅-C₆ cycloalkyl group.

Even more preferably each R₇ independently represents cyano, halogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₃ alkynyl, C₁-C₄ alkylthio or C₃-C₄cycloalkyl; m is 0, 1 or 2.

More preferably still each R₇ independently represents cyano, halogen,C₁-C₃ alkyl, C₁-C₃ haloalkyl or C₃-C₄ cycloalkyl; m is 0, 1 or 2.

Most preferably each R₇ independently represents fluoro, chloro or C₁-C₃alkyl; m is 1 or 2.

Preferably R_(a) is selected from hydrogen, C₁-C₆ alkyl, C₃-C₇cycloalkyl, C₃-C₆ alkenyl and C₃-C₆ alkynyl, in which the alkyl,cycloalkyl, alkenyl and alkynyl groups may be optionally substitutedwith 1 to 3 substituents independently selected from halogen, C₁-C₆alkoxy and C₁-C₆ alkylthio.

More preferably R_(a) is selected from hydrogen, C₁-C₄ alkyl and C₃-C₅cycloalkyl, in which the alkyl and cycloalkyl groups may be optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, C₁-C₃ alkoxy and C₁-C₃ alkylthio.

Even more preferably R_(a) is selected from hydrogen and C₁-C₄ alkyl, inwhich the alkyl group may be optionally substituted with 1 to 3 halogenatoms.

Most preferably R_(a) is selected from hydrogen and C₁-C₃ alkyl, inwhich the alkyl group may be optionally substituted with 1 to 3 fluoroatoms.

Preferably R_(b) and R_(c) are each independently selected fromhydrogen, halogen, cyano, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio, in which the alkyl,cycloalkyl, alkenyl and alkynyl groups may be optionally substitutedwith 1 to 3 substituents independently selected from halogen, C₁-C₆alkoxy and C₁-C₆ alkylthio.

A preferred group of compounds according to the invention are those offormula IA:

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, Ra, Rb, Rc, n and m are asdefined for compounds of formula I, or a salt or N-oxide thereof.Preferred definitions of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, Ra, Rb, Rc, nand m are as defined for compounds of formula I.

Another preferred group of compounds according to the invention arethose of formula IB which are compounds of formula I wherein R₁ and R₂are each independently selected from hydrogen, C₁-C₆ alkyl and C₃-C₇cycloalkyl, in which the alkyl and cycloalkyl groups may be optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio; or

R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₆ cycloalkyl group (which may be optionally substitutedwith 1 to 3 substituents independently selected from the groupconsisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio);

R₃ and R₄ are each independently selected from hydrogen, halogen,hydroxyl, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₃-C₇ cycloalkyl, in which thealkyl, alkoxy and cycloalkyl groups may be optionally substituted with 1to 3 substituents independently selected from halogen, C₁-C₆ alkoxy andC₁-C₆ alkylthio; or

R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a), C═C(R_(b))(R_(c)) or C₃-C₆ cycloalkyl (whichmay be optionally substituted with 1 to 3 substituents independentlyselected from the group consisting of a halogen, C₁-C₆ alkyl, C₁-C₆alkoxy and C₁-C₆ alkylthio); or

R₂ and R₃ together with the carbon atoms to which they are attachedrepresent a C₅-C₇ cycloalkyl (which may be optionally substituted with 1to 3 substituents independently selected from the group consisting ofhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio, and,additionally, a ring carbon unit may be replaced by an oxygen or sulphuratom);

each R₅ independently represents halogen, cyano, C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆alkenyloxy, C₃-C₆ alkynyloxy, C₁-C₆ alkylthio, —C(═NOR_(a))C₁-C₆alkyl,phenyl, heteroraryl (wherein heteroaryl is pyridyl, thiophenyl,thiazolyl, imidazolyl or oxazolyl), phenoxy or heteroraryloxy (whereinheteroaryl is pyridyl, thiophenyl, thiazolyl, imidazolyl or oxazolyl),in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, phenyl and heteroaryl groups may be optionally substitutedwith 1 to 5 substituents independently selected from halogen, C₁-C₆alkyl, C₁-C₆ alkoxy, cyano and C₁-C₆ alkylthio; n is 0, 1, 2, 3 or 4;

R₆ is hydrogen, halogen or C₁-C₆ alkyl;

each R₇ independently represents cyano, halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkenyl, C₃-C₆haloalkynyl, C₁-C₆ alkylthio, C₁-C₆ haloalkoxy, C₁-C₆ haloalkylthio,C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆alkenyloxy or C₃-C₆ alkynyloxy; mis 0, 1, 2, 3 or 4; or

Two adjacent R₇ substituents together with the carbon atoms to whichthey are attached represent a C₅-C₇ cycloalkyl group (which may beoptionally substituted with 1 to 3 substituents independently selectedfrom the group consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy andC₁-C₆ alkylthio, and, additionally, a ring carbon unit may be replacedby an oxygen or sulphur atom);

R_(a) is selected from hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₃-C₆alkenyl and C₃-C₆ alkynyl, in which the alkyl, cycloalkyl, alkenyl andalkynyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio;

R_(b) and R_(c) are each independently selected from hydrogen, halogen,cyano, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₁-C₆ alkoxy and C₁-C₆ alkylthio, in which the alkyl, cycloalkyl,alkenyl and alkynyl groups may be optionally substituted with 1 to 3substituents independently selected from halogen, C₁-C₆ alkoxy and C₁-C₆alkylthio; or a salt or N-oxide thereof.

Another preferred group of compounds according to the invention arethose of formula IC which are compounds of formula I wherein R₁ and R₂are each independently selected from hydrogen and C₁-C₄ alkyl, in whichthe alkyl group may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₃ alkoxy and C₁-C₃ alkylthio;or

R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₆ cycloalkyl group (which may be optionally substitutedwith 1 to 3 substituents independently selected from the groupconsisting of halogen, C₁-C₃ alkyl, C₁-C₃ alkoxy and C₁-C₃ alkylthio);

R₃ and R₄ are each independently selected from hydrogen, halogen, C₁-C₄alkyl and C₃-C₄ cycloalkyl, in which the alkyl and cycloalkyl groups maybe optionally substituted with 1 to 3 substituents independentlyselected from halogen, C₁-C₃ alkoxy and C₁-C₃ alkylthio; or

R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a), or C₃-C₆ cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of a halogen, C₁-C₃ alkyl, C₁-C₃ alkoxy and C₁-C₃alkylthio);

each R₅ independently represents halogen, cyano, C₁-C₄ alkyl, C₃-C₄cycloalkyl, C₁-C₃ alkoxy, C₃-C₆ alkenyloxy, C₃-C₆ alkynyloxy, C₁-C₃alkylthio, —C(═NOR_(a))C₁-C₆alkyl, phenyl, heteroraryl (whereinheteroaryl is pyridyl, thiazolyl or oxazolyl), in which the alkyl,cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, phenyl and heteroaryl groupsmay be optionally substituted with 1 to 3 substituents independentlyselected from halogen, C₁-C₃ alkyl and C₁-C₃ alkoxy; n is 0, 1 or 2;

R₆ is hydrogen or C₁-C₃ alkyl;

each R₇ independently represents cyano, halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₂-C₆ alkynyl, C₁-C₆ alkylthio, C₁-C₆ haloalkoxy, C₁-C₆haloalkylthio, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆ alkenyloxy or C₃-C₆alkynyloxy; m is 0, 1, 2 or 3; or

Two adjacent R₇ substituents together with the carbon atoms to whichthey are attached represent a C₅-C₆ cycloalkyl group;

R_(a) is selected from hydrogen, C₁-C₄ alkyl and C₃-C₅ cycloalkyl, inwhich the alkyl and cycloalkyl groups may be optionally substituted with1 to 3 substituents independently selected from halogen, C₁-C₃ alkoxyand C₁-C₃ alkylthio;

or a salt or N-oxide thereof.

Another preferred group of compounds according to the invention arethose of formula ID which are compounds of formula I wherein R₁ and R₂are each independently selected from hydrogen and C₁-C₄ alkyl, in whichthe alkyl group may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, methoxy and methylthio; or

R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₄ cycloalkyl group (which may be optionally substitutedwith 1 to 3 substituents independently selected from the groupconsisting of halogen and C₁-C₃ alkyl);

R₃ and R₄ are each independently selected from hydrogen, halogen andC₁-C₄ alkyl, in which the alkyl group may be optionally substituted with1 to 3 substituents independently selected from halogen, methoxy andmethylthio; or

R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a) or C₃-C₄ cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of a halogen and C₁-C₃ alkyl);

each R₅ independently represents halogen, cyano, C₁-C₄ alkyl, C₃-C₄cycloalkyl or phenyl, in which the alkyl, cycloalkyl and phenyl groupsmay be optionally substituted with 1 to 3 substituents independentlyselected from halogen or C₁-C₃ alkyl; n is 0, 1 or 2;

R₆ is hydrogen or methyl;

each R₇ independently represents cyano, halogen, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₂-C₃ alkynyl, C₁-C₄ alkylthio or C₃-C₄ cycloalkyl; m is 0, 1or 2; and

R₈ is selected from hydrogen and C₁-C₄ alkyl, in which the alkyl groupmay be optionally substituted with 1 to 3 halogen atoms;

or a salt or N-oxide thereof.

Another preferred group of compounds according to the invention arethose of formula IE which are compounds of formula I wherein R₁ and R₂are each independently selected from hydrogen and C₁-C₃ alkyl; or

R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₄ cycloalkyl group;

R₃ and R₄ are each independently selected from hydrogen, halogen andC₁-C₃ alkyl; or

R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a) or C₃-C₄ cycloalkyl;

each R₅ independently represents halogen, cyano, C₁-C₃ alkyl, C₃-C₄cycloalkyl or phenyl, in which the alkyl, cycloalkyl and phenyl groupsmay be optionally substituted with 1 to 3 halogen atoms; n is 0, 1 or 2;

R₆ is hydrogen or methyl;

each R₇ independently represents cyano, halogen, C₁-C₃ alkyl, C₁-C₃haloalkyl or C₃-C₄ cycloalkyl; m is 0, 1 or 2; and

R_(a) is selected from hydrogen and C₁-C₃ alkyl, in which the alkylgroup may be optionally substituted with 1 to 3 fluoro atoms;

or a salt or N-oxide thereof.

Another preferred group of compounds according to the invention arethose of formula IF which are compounds of formula I wherein R₁ and R₂are each independently selected from hydrogen and C₁-C₃ alkyl; or

R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₄ cycloalkyl group;

R₃ and R₄ are each independently selected from hydrogen, fluoro or C₁-C₃alkyl; or R₃ and R₄ together with the carbon atom to which they areattached represent C═O or C₃-C₄ cycloalkyl;

each R₅ independently represents halogen, C₁-C₃ alkyl or C₃-C₄cycloalkyl, in which the alkyl and cycloalkyl groups may be optionallysubstituted with 1 to 3 fluoro atoms; n is 0, 1 or 2;

R₆ is hydrogen; and

each R₇ independently represents fluoro, chloro or C₁-C₃ alkyl; m is 1or 2;

or a salt or N-oxide thereof.

Specific examples of compounds of formula I are illustrated in theTables A1 to A18 below:

TABLE A1 provides 170 compounds of formula I-a

(I-a)wherein R₆, R₇a and R₇b are all Hand wherein the values of R₁, R₂, R₃, R₄, and R₅ are as defined in TableZ1 below:

TABLE Z1 Entry R₁ R₂ R₃ R₄ R₅ 1 CH₃ CH₃ H H H [n = 0] 2 CH₃ CH₃ H H 5-F3 CH₃ CH₃ H H 6-F 4 CH₃ CH₃ H H 7-F 5 CH₃ CH₃ H H 8-F 6 CH₃ CH₃ H H 5-Cl7 CH₃ CH₃ H H 6-Cl 8 CH₃ CH₃ H H 7-Cl 9 CH₃ CH₃ H H 8-Cl 10 CH₃ CH₃ H H5-Br 11 CH₃ CH₃ H H 6-Br 12 CH₃ CH₃ H H 5-I 13 CH₃ CH₃ H H 5,6-F₂ 14 CH₃CH₃ H H 5,6-Cl₂ 15 CH₃ CH₃ H H 5-F-6-Cl 16 CH₃ CH₃ H H 5-CH₃ 17 CH₃ CH₃H H 6-CH₃ 18 CH₃ CH₃ H H 5-CH₂CH₃ 19 CH₃ CH₃ H H 5-cyclopropyl 20 CH₃CH₃ H H 5-CN 21 CH₃ CH₃ H H 5-OCH₃ 22 CH₃ CH₃ H H 5-OC₆H₅ 23 CH₃ CH₃ H H5-O-(pyrid-2-yl) 24 CH₃ CH₃ H H 5-CF₃ 25 CH₃ CH₃ H H 5-(2-F—C₆H₅) 26 CH₃CH₃ H H 5-(thiazol-2-yl) 27 CH₃ CH₃ H CH₃ H [n = 0] 28 CH₃ CH₃ H CH₃ 5-F29 CH₃ CH₃ H OCH₃ H [n = 0] 30 CH₃ CH₃ H OCH₃ 5-F 31 CH₃ CH₃ H F H [n =0] 32 CH₃ CH₃ H F 5-F 33 CH₃ CH₃ H F 6-F 34 CH₃ CH₃ H F 5-Cl 35 CH₃ CH₃H F 6-Cl 36 CH₃ CH₃ H F 5-Br 37 CH₃ CH₃ CH₃ CH₃ H [n = 0] 38 CH₃ CH₃ CH₃CH₃ 5-F 39 CH₃ CH₃ CH₃ CH₃ 6-F 40 CH₃ CH₃ CH₃ CH₃ 7-F 41 CH₃ CH₃ CH₃ CH₃8-F 42 CH₃ CH₃ CH₃ CH₃ 5-Cl 43 CH₃ CH₃ CH₃ CH₃ 6-Cl 44 CH₃ CH₃ CH₃ CH₃7-Cl 45 CH₃ CH₃ CH₃ CH₃ 8-Cl 46 CH₃ CH₃ CH₃ CH₃ 5-Br 47 CH₃ CH₃ CH₃ CH₃6-Br 48 CH₃ CH₃ CH₃ CH₃ 5,6-F2 49 CH₃ CH₃ CH₃ CH₃ 5,6-Cl2 50 CH₃ CH₃ CH₃CH₃ 5-F-6-Cl 51 CH₃ CH₃ CH₃ CH₃ 5-CH3 52 CH₃ CH₃ CH₃ CH₃ 6-CH3 53 CH₃CH₃ CH₃ CH₃ 5-CH2CH3 54 CH₃ CH₃ CH₃ CH₃ 5-cyclopropyl 55 CH₃ CH₃ CH₃ CH₃5-CN 56 CH₃ CH₃ CH₃ CH₃ 5-OC6H5 57 CH₃ CH₃ CH₃ CH₃ 5-O-(pyrid-2-yl) 58CH₃ CH₃ CH₃ CH₃ 5-CF3 59 CH₃ CH₃ CH₃ CH₃ 5-(2-F—C6H5) 60 CH₃ CH₃ CH₃ CH₃5-(thiazol-2-yl) 61 CH₃ CH₃ ═O H [n = 0] 62 CH₃ CH₃ ═O 5-F 63 CH₃ CH₃ ═O6-F 64 CH₃ CH₃ ═O 5-Cl 65 CH₃ CH₃ ═O 6-Cl 66 CH₃ CH₃ ═O 5-Br 67 CH₃ CH₃═O 5-CH₃ 68 CH₃ CH₃ ═O 5-C₂H₅ 69 CH₃ CH₃ ═O 5-C₆H₅ 70 CH₃ CH₃ ═NOH H [n= 0] 71 CH₃ CH₃ ═NOH 5-CH₃ 72 CH₃ CH₃ ═NOH 5-C₂H₅ 73 CH₃ CH₃ ═NOH 5-C₆H₅74 CH₃ CH₃ ═NOCH₃ H [n = 0] 75 CH₃ CH₃ ═NOCH₃ 5-F 76 CH₃ CH₃ ═NOCH₃ 6-F77 CH₃ CH₃ ═NOCH₃ 5-Cl 78 CH₃ CH₃ ═NOCH₃ 6-Cl 79 CH₃ CH₃ ═NOCH₃ 5-Br 80CH₃ CH₃ ═NOCH₃ 5-CH₃ 81 CH₃ CH₃ ═NOCH₃ 5-C₂H₅ 82 CH₃ CH₃ ═NOCH₃ 5-C₆H₅83 CH₃ CH₃ F F H [n = 0] 84 CH₃ CH₃ F F 5-F 85 CH₃ CH₃ F F 6-F 86 CH₃CH₃ F F 5-Cl 87 CH₃ CH₃ F F 6-Cl 88 CH₃ CH₃ F F 5-Br 89 CH₃ CH₃ F F5-F-6-Cl 90 CH₃ CH₃ F F 5-CH₃ 91 CH₃ CH₃ cyclopropyl H [n = 0] 92 CH₃CH₃ cyclopropyl 5-F 93 CH₃ CH₃ cyclopropyl 5-Cl 94 CH₃ CH₃ cyclopropyl5-CH₃ 95 CH₃ CH₃ cyclopropyl 5,6-F₂ 96 CH₃ CH₃ cyclopropyl 5-F,6-Cl 97CH₃ CH₃ cyclobutyl H [n = 0] 98 CH₃ CH₃ cyclobutyl 5-F 99 CH₃ CH₃cyclobutyl 5-Cl 100 CH₃ CH₃ cyclobutyl 5-CH₃ 101 CH₃ CH₃ cyclobutyl5,6-F₂ 102 CH₃ CH₃ cyclobutyl 5-F,6-Cl 103 CH₃ CH₃ cyclopentyl H [n = 0]104 CH₃ CH₃ cyclopentyl 5-F 105 H H cyclopropyl H [n = 0] 106 H Hcyclopropyl 5-F 107 H H cyclopropyl 5-Cl 108 H H cyclopropyl 5-CH₃ 109 HH cyclopropyl 5,6-F₂ 110 H H cyclopropyl 5-F,6-Cl 111 H H cyclobutyl H[n = 0] 112 H H cyclobutyl 5-F 113 H H cyclobutyl 5-Cl 114 H Hcyclobutyl 5-CH₃ 115 H H cyclobutyl 5,6-F₂ 116 H H cyclobutyl 5-F,6-Cl117 H H cyclopentyl H [n = 0] 118 H H cyclopentyl 5-F 119 CH₃ CH₂OH₃ H HH [n = 0] 120 CH₃ CH₂OH₃ H H 5-F 121 CH₃ CH₂OH₃ H H 5-Cl 122 CH₂OH₃CH₂OH₃ H H H [n = 0] 123 CH₂OH₃ CH₂OH₃ H H 5-F 124 CH₂OH₃ CH₂OH₃ H H5-Cl 125 CH₃ CF₃ H H H [n = 0] 126 CH₃ CF3 H H 5-F 127 CH₃ CH₂Cl H H H[n = 0] 128 CH₃ CH₂Cl H H 5-F 129 CH₃ CH₂Cl CH₃ CH₃ H [n = 0] 130 CH₃CH₂Cl CH₃ CH₃ 5-F 131 CH₃ CH₂OCH₃ CH₃ CH₃ H [n = 0] 132 CH₃ CH₂OCH₃ CH₃CH₃ 5-F 133 CH₃ CH₂SCH₃ CH₃ CH₃ H [n = 0] 134 CH₃ CH₂SCH₃ CH₃ CH₃ 5-F135 CH₃ H H H H [n = 0] 136 CH₃ H H H 5-F 137 CH₃ CH₂CH₂CH₃ H H H [n =0] 138 CH₃ CH₂CH₂OH₃ H H 5-F 139 cyclopropyl H H H [n = 0] 140cyclopropyl CH₃ CH₃ H [n = 0] 141 cyclopropyl ═O H [n = 0] 142cyclopropyl F F H [n = 0] 143 cyclopropyl cyclopropyl H [n = 0] 144cyclopropyl H H 5-F 145 cyclopropyl CH₃ CH₃ 5-F 146 cyclopropyl ═O 5-F147 cyclopropyl F F 5-F 148 cyclopropyl cyclopropyl 5-F 149 cyclopropylH H 5-Cl 150 cyclopropyl H H 5-Br 151 cyclobutyl H H H [n = 0] 152cyclobutyl ═O H [n = 0] 153 cyclobutyl F F H [n = 0] 154 cyclobutyl H H5-F 155 cyclobutyl ═O 5-F 156 cyclobutyl F F 5-F 157 cyclobutyl H H 5-Cl158 cyclobutyl H H 5-Br 159 cyclopentyl H H H [n = 0] 160 cyclopentyl ═OH [n = 0] 161 cyclopentyl F F H [n = 0] 162 cyclopentyl H H 5-F 163cyclopentyl ═O 5-F 164 cyclopentyl F F 5-F 165 cyclohexyl H H H [n = 0]166 cyclohexyl ═O H [n = 0] 167 cyclohexyl F F H [n = 0] 168 cyclohexylH H 5-F 169 cyclohexyl ═O 5-F 170 cyclohexyl F F 5-FTable A2 provides 170 compounds of formula Ia wherein R₇a and R₇b are H,R₆ is methyl and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A3 provides 170 compounds of formula Ia wherein R₇a and R₇b are H,R₆ is Chloro and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A4 provides 170 compounds of formula Ia wherein R₆ and R₇b are H,R₇a is methyl and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A5 provides 170 compounds of formula Ia wherein R₆ and R₇b are H,R₇a is fluoro and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A6 provides 170 compounds of formula Ia wherein R₆ and R₇b are H,R₇a is chloro and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A7 provides 170 compounds of formula Ia wherein R₆ and R₇b are H,R₇a is ethyl and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A8 provides 170 compounds of formula Ia wherein R₆ and R₇b are H,R₇a is bromo and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A9 provides 170 compounds of formula Ia wherein R₆ is H, R₇a andR₇b are methyl and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A10 provides 170 compounds of formula Ia wherein R₆ is H, R₇a andR₇b are chloro and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.Table A11 provides 170 compounds of formula Ia wherein R₆ is H, R₇a ismethyl, R₇b is chloro and wherein the values of R₁, R₂, R₃, R₄ and R₅are as defined in Table Z1 above.Table A12 provides 170 compounds of formula Ia wherein R₆ is H, R₇a isfluoro, R₇b is methyl and wherein the values of R₁, R₂, R₃, R₄ and R₅are as defined in Table Z1 above.Table A13 provides 170 compounds of formula Ia wherein R₆ is H, R₇a isfluoro, R₇b is chloro and wherein the values of R₁, R₂, R₃, R₄ and R₅are as defined in Table Z1 above.Table A14 provides 170 compounds of formula Ia wherein R₆ is H, R₇a ismethyl, R₇b is fluoro and wherein the values of R₁, R₂, R₃, R₄ and R₅are as defined in Table Z1 above.Table A15 provides 170 compounds of formula Ia wherein R₆ is H, R₇a ischloro, R₇b is methyl and wherein the values of R₁, R₂, R₃, R₄ and R₅are as defined in Table Z1 above.Table A16 provides 170 compounds of formula Ia wherein R₆ is H, R₇a ischloro, R₇b is fluoro and wherein the values of R₁, R₂, R₃, R₄ and R₅are as defined in Table Z1 above.Table A17 provides 170 compounds of formula Ia wherein R₆ is H, R₇a andR₇b is —CH₂CH₂CH₂— and wherein the values of R₁, R₂, R₃, R₄ and R₅ areas defined in Table Z1 above.Table A18 provides 170 compounds of formula Ia wherein R₆ and R₇a are H,R₇b is methyl and wherein the values of R₁, R₂, R₃, R₄ and R₅ are asdefined in Table Z1 above.

Compounds according to the invention may possess any number of benefitsincluding, inter alia, advantageous levels of biological activity forprotecting plants against diseases that are caused by fungi or superiorproperties for use as agrochemical active ingredients (for example,greater biological activity, an advantageous spectrum of activity, anincreased safety profile, improved physico-chemical properties, orincreased biodegradability).

Compounds of the present invention can be made as shown in the followingschemes, in which, unless otherwise stated, the definition of eachvariable is as defined above for a compound of formula (I).

The compounds of formula I, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, m and nare as defined for compounds of formula I, can be obtained bytransformation of a compound of formula II, wherein R₆, R₇ and m are asdefined for compounds of formula I, with a compound of formula III,wherein R₁, R₂, R₃, R₄, R₅ and n are as defined for compounds of formulaI and

Hal is halogen, preferably chloro or bromo, in the presence of anorganic base such as triethylamine, ethyldiisopropylamine, pyridine or2,6-lutidine or in the presence of a transition metal catalyst such as acopper-based catalyst such as copper (I) acetylacetonate or copper (I)bromide-1,10-phenanthroline complex, a nickel catalyst such asDichloro(1,3-bis(diphenylphosphino)propane)nickel or a palladium-basedcatalyst such asChloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II),X-Phos aminobiphenyl palladium chloride precatalyst or[1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II)dichloride in an aprotic solvent such as pyridine, toluene orN,N-dimethylformamide while heating. This is shown in Scheme 1.

The compounds of formula II, wherein R₆, R₇ and m are as defined forcompounds of formula I, are either commercially available or easilyprepared using the methods known by persons who are skilled in the artas described in the literature (Grimmet, M. R. In Imidazole andBenzimidazole Synthesis; Meth-Cohn, Katritzky, Eds.; Elsevier Science:Oxford, 1997).

The compounds of formula III, wherein R₁, R₂, R₃, R₄, R₅ and n are asdefined for compounds of formula I and Hal is halogen, preferably chloroor bromo, can be obtained by transformation of a compound of formula IV,wherein R₁, R₂, R₃, R₄, R₅ and n are as defined for compounds of formulaI, with a halogenating reagent, such as phosphorus oxychloridephosphorus oxybromide, thionyl chloride, thionyl bromide or Vilsmeierreagent neat or in the presence a solvent such as dichloromethane atvarious temperatures ranging form cooling to heating. This is shown inScheme 2.

The compounds of formula IV, wherein R₁, R₂, R₃, R₄, R₅ and n are asdefined for compounds of formula I, can be obtained by transformation ofa compound of formula V, wherein R₁, R₂, R₃, R₄, R₅ and n are as definedfor compounds of formula I and R₈ is C₁-C₆ alkyl, with sodium acetate inacetic acid as described in the literature (Yu. B. Vikharev et al.Pharmaceutical Chemistry Journal, 2005, 39, 405-408). This is shown inScheme 3.

Alternatively, the compounds of formula III, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I and Hal is halogen,preferably chloro or bromo, can be obtained by transformation of acompound of formula V, wherein R₁, R₂, R₃, R₄, R₅ and n are as definedfor compounds of formula I and R₈ is C₁-C₆ alkyl, with a halogenatingreagent, such as sulfuryl chloride as described in the literature (TaeboSim et al. Tetrahedron Letters, 2010, 51, 4609). This is shown in Scheme4.

The compounds of formula V, wherein R₁, R₂, R₃, R₄, R₅ and n are asdefined for compounds of formula I and R₈ is C₁CO₆ alkyl, can beobtained by transformation of a compound of formula VI-a, VI-b or VI-c,wherein R₁, R₂, R₃, R₄, R₅ and n are as defined for compounds of formulaI and R′ is either H or C₁-C₆ alkyl, with a C₁-C₆ alkyl thiocyanateunder acidic conditions, e.g. with sulfuric acid as described in theliterature (Yu. B. Vikharev et al. Pharmaceutical Chemistry Journal,2005, 39, 405408). This is shown in Scheme 5.

The compounds of formula VI-a, VI-b or VI-c, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I and R′ is either H orC₁-C₆ alkyl, are either commercially available or easily prepared usingthe methods known by persons who are skilled in the art.

Alternatively, the compounds of formula IV, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I, can be obtained bytransformation of a compound of formula VII, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I, under acidicconditions, e.g. with sulfuric acid or polyphosphoric acid as describedin the literature (Jun-ichi Minamikawa, Bioorganic & MedicinalChemistry, 2003, 11, 2205-2209). This is shown in Scheme 6.

The compounds of formula VII, wherein R₁, R₂, R₃, R₄, R₅ and n are asdefined for compounds of formula I, can be obtained by transformation ofa compound of formula VIII, wherein R₁, R₂, R₃, R₄, R₅ and n are asdefined for compounds of formula I, upon treatment with hydroxylamine orhydroxylamine hydrochloride in a solvent such as ethanol or pyridine inthe presence or absence of a base such as sodium acetate at temperaturesranging from ambient temperature to heating. This is shown in Scheme 7.

The compounds of formula VIII, wherein R₁, R₂, R₃, R₄, R₅ and n are asdefined for compounds of formula I, are either commercially available oreasily prepared using the methods known by persons who are skilled inthe art.

Alternatively, the compounds of formula IV, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I, can be obtained bytransformation of a compound of formula IX-a, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I, upon treatment withcarbonylating agents such as phosgene, triphosgene or carbonyldiimidazole and subsequent heating or utilizing directed catalytic C—Hactivation—carbonylation in the presence of carbon monoxide gas, apalladium catalyst such as palladium acetate and an oxidant suchbenzoquinone as reported in the literature (Jaume Granell et al. Chem.Commun., 2011, 47, 1054-1056). This is shown in Scheme 8.

Alternatively, the compounds of formula IV, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I, can be obtained bytransformation of a compound of formula IX-b, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I and Hal is halogen,preferably chloro, bromo, or iodo, utilizing an intramolecularaminocarbonylation in the presence of carbon monoxide gas, a palladiumcatalyst such as Dichlorobis(tricyclohexylphosphine)palladium(II) orDichlorobis(triphenlphosphine) palladium(II) and an organic base such astriethyl amine, pyrrolidine or an inorganic base such cesium carbonte orpotassium carbonate as reported in the literature (Ruimao Hua et al.Tetrahedron Letters, 2013, 54, 5159-5161). This is shown in Scheme 9.

Alternatively, the compounds of formula IV, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I, can be obtained bytransformation of a compound of formula X, wherein R₁, R₂, R₃, R₄, R₅and n are as defined for compounds of formula I and R₉ is C₁-C₆ alkyl,under acid conditions e.g. sulfuric acid or triflic acid as described inthe literature (Tomohiko Ohwada et al. Journal of Organic Chemistry,2012, 77, 9313). This is shown in Scheme 10.

The compounds of formula I-b, wherein R₃ and R₄ are fluoro and R₁, R₂,R₅, R₆, R₇, m and n are as defined for compounds of formula I, can beobtained by transformation of a compound of formula I-c wherein R₃ andR₄ together with the carbon atom to which they are attached representC═O and R₁, R₂, R₅, R₆, R₇, m and n are as defined for formula I with afluorinating agent such as diethylaminosulfur trifluoride (DAST) or2,2-difluoro-1,3-dimethyl-imidazolidine (DFI) neat or in the presence ofa solvent while heating. This is shown in Scheme 11.

The compounds of formula I-c, wherein R₃ and R₄ together with the carbonatom to which they are attached represent C═O and R₁, R₂, R₅, R₆, R₇, mand n are as defined for formula I, can be obtained by transformation ofa compound of formula II, wherein R₆, R₇ and m are as defined forcompounds of formula I, with a compound of formula III-a, wherein R₃ andR₄ together with the carbon atom to which they are attached representC═O and R₁, R₂, R₅ and n are as defined for formula I and Hal ishalogen, preferably chloro or bromo, in the presence of a hinderedorganic base such as triethylamine, ethyldiisopropylamine, pyridine or2,6-lutidine or in the presence of a transition metal catalyst such as acopper-based catalyst such as copper (I) acetylacetonate or copper (I)bromide-1,10-phenanthroline complex, a nickel catalyst such asDichloro(1,3-bis(diphenylphosphino)propane)nickel or a palladium-basedcatalyst such asChloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II),X-Phos aminobiphenyl palladium chloride precatalyst or[1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II)dichloride in an aprotic solvent such as pyridine, toluene orN,N-dimethylformamide while heating. This is shown in Scheme 12.

The compounds of formula III-a, wherein R₃ and R₄ together with thecarbon atom to which they are attached represent C═O and R₁, R₂, R₅ andn are as defined for formula I and Hal is halogen, preferably chloro orbromo, can be obtained by transformation of a compound of formula IV-a,wherein wherein R₃ and R₄ together with the carbon atom to which theyare attached represent C═O and R₁, R₂, R₅ and n are as defined forformula I, with a halogenating reagent, such as phosphorus oxychloridephosphorus oxybromide, thionyl chloride, thionyl bromide or Vilsmeierreagent neat or in the presence a solvent such as dichloromethane atvarious temperatures ranging form cooling to heating. This is shown inScheme 13.

The compounds of formula IV-a, wherein R₃ and R₄ together with thecarbon atom to which they are attached represent C═O and R₁, R₂, R₅ andn are as defined for formula I, can be obtained by transformation of acompound of formula IV-b, wherein R₃ represents hydrogen, R₄ representsOH and R₁, R₂, R₅ and n are as defined for formula I, with an oxidizingagent such as 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol3(1H)-one(Dess-Martin periodinane) or using oxalyl chloride, dimethyl sulfoxide(DMSO) and an organic base, such as triethylamine (Swern oxidation).This is shown in Scheme 14.

The compounds of formula IV-b, wherein R₃ represents hydrogen, R₄represents OH and R₁, R₂, R₅ and n are as defined for formula I, can beobtained by transformation of a compound of formula IV-c, wherein R₃represents hydrogen, R₄ represents Hal, wherein Hal is halogen,preferably chloro or bromo, and R₁, R₂, R₅ and n are as defined forformula I, under hydrolysis conditions such as heating in a mixture ofan organic solvent such as tetrahydrofuran or 1,4-dioxane and water inthe presence or absence of an inorganic acid such as hydrochloric acidor an inorganic base such as sodium hydrogencarbonate at temperaturesranging from ambient temperature to heating. This is shown in Scheme 15.

The compounds of formula IV-c, wherein R₃ represents hydrogen, R₄represents Hal, wherein Hal is halogen, preferably chloro or bromo, andR₁, R₂, R₅ and n are as defined for formula I, can be obtained bytransformation of a compound of formula IV-d, wherein R₃ and R₄represent hydrogen and R₁, R₂, R₅ and n are as defined for formula I,with a halogenating agent such as N-chloro succinimide (NCS), N-bromosuccinimide (NBS) or 1,3-dibromo-5,5-dimethylhydantoin in the presenceof a radical initiator such as benzoyl peroxide orazobisisobutyronitrile (AIBN) as described in the literature (Jahangiret al Journal of Organic Chemistry, 1989, 54, 2992). This is shown inScheme 16.

Alternatively, the compounds of formula IV-a, wherein R₃ and R₄ togetherwith the carbon atom to which they are attached represent C═O and R₁,R₂, R₅ and n are as defined for formula I, can be obtained bytransformation of a compound of formula IV-e, wherein R₃ and R₄represent Hal, wherein Hal is halogen, preferably chloro or bromo, andR₁, R₂, R₅ and n are as defined for formula I, under hydrolysisconditions such as heating in a mixture of an organic solvent such astetrahydrofuran or 1,4-dioxane and water in the presence or absence ofan inorganic acid such as hydrochloric acid or an inorganic base such assodium hydrogencarbonate at temperatures ranging from ambienttemperature to heating. This is shown in Scheme 17.

The compounds of formula IV-e, wherein R₃ and R₄ represent Hal, whereinHal is halogen, preferably chloro or bromo, and R₁, R₂, R₅ and n are asdefined for formula I, can be obtained by transformation of a compoundof formula IV-d, wherein R₃ and R₄ represent hydrogen and R₁, R₂, R₅ andn are as defined for formula I, with a halogenating agent such asN-chloro succinimide (NCS), N-bromo succinimide (NBS) or1,3-dibromo-5,5-dimethylhydantoin in the presence of a radical initiatorsuch as benzoyl peroxide or azobisisobutyronitrile (AIBN) as describedin the literature (Jahangir et al Journal of Organic Chemistry, 1989,54, 2992). This is shown in Scheme 18.

The compounds of formula IV-d can be obtained according to the methoddescribed in Scheme 3.

Alternatively, the compounds of formula I-a, wherein R₃ and R₄ arefluoro and R₁, R₂, R₅, R₆, R₇, m and n are as defined for compounds offormula I, can be obtained by transformation of a compound of formulaII, wherein R₆, R₇ and m are as defined for compounds of formula I, witha compound of formula III-b, wherein R₃ and R₄ are fluoro and R₁, R₂, R₅and n are as defined for formula I and Hal is halogen, preferably chloroor bromo, in the presence of a hindered organic base such astriethylamine, ethyldiisopropylamine, pyridine or 2,6-lutidine or in thepresence of a transition metal catalyst such as a copper-based catalystsuch as copper (I) acetylacetonate or copper (I)bromide-1,10-phenanthroline complex, a nickel catalyst such asDichloro(1,3-bis(diphenylphosphino)propane)nickel or a palladium-basedcatalyst such asChloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II),X-Phos aminobiphenyl palladium chloride precatalyst or[1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II)dichloride in an aprotic solvent such as pyridine, toluene orN,N-dimethylformamide while heating. This is shown in Scheme 19.

The compounds of formula III-b, wherein R₃ and R₄ are fluoro and R₁, R₂,R₅ and n are as defined for compounds of formula I and Hal is halogen,preferably chloro or bromo, can be obtained by transformation of acompound of formula IV-f, wherein R₃ and R₄ are fluoro and R₁, R₂, R₅and n are as defined for compounds of formula I, with a halogenatingreagent, such as phosphorus oxychloride phosphorus oxybromide, thionylchloride, thionyl bromide or Vilsmeier reagent neat or in the presence asolvent such as dichloromethane at various temperatures ranging formcooling to heating. This is shown in Scheme 20.

The compounds of formula IV-f, wherein R₃ and R₄ are fluoro and R₁, R₂,R₅ and n are as defined for compounds of formula I, can be obtained bytransformation of a compound of formula IV-e, wherein R₃ and R₄ are Haland Hal is halogen, preferably chloro or bromo, and R₁, R₂, R₅ and n areas defined for compounds of formula I, with a fluoride source, such aspotassium fluoride, cesium fluoride or hydrogen fluoride in the presenceof an organic base such as pyridine or triethylamine as described in theliterature (Hideki Umetani et al. WO 2013047749). This is shown inScheme 21.

Alternatively, the compounds of formula I, wherein R₁, R₂, R₃, R₄, R₅,R₆, R₇, m and n are as defined for formula I, can be obtained bytransformation of a compound of formula I-d, wherein R₁, R₂, R₃, R₄, R₆,R₇, m and n are as defined for formula I and Z represents bromine oriodine in a solvent, in the presence of or absence of a base, and in thepresence of a coupling reagent and a metal catalyst. There are noparticular limitations on the coupling agent, catalyst, solvent andbases, provided it is used in ordinary coupling reactions, such as thosedescribed in “Cross-Coupling Reactions: A Practical Guide (Topics inCurrent Chemistry)”, edited by Norio Miyaura and S. L. Buchwald(editions Springer), or “Metal-Catalyzed Cross-Coupling Reactions”,edited by Armin de Meijere and François Diederich (editions WILEY-VCH).This is shown in Scheme 22.

Alternatively, the compounds of formula I, wherein R₁, R₂, R₃, R₄, R₅,R₆, R₇, m and n are as defined for formula I, can be obtained bytransformation of a compound of formula I-e, wherein R₁, R₂, R₃, R₄, R₅,R₆, m and n are as defined for formula I and Y represents bromine oriodine in a solvent, in the presence of or absence of a base, and in thepresence of a coupling reagent and a metal catalyst. There are noparticular limitations on the coupling agent, catalyst, solvent andbases, provided it is used in ordinary coupling reactions, such as thosedescribed in “Cross-Coupling Reactions: A Practical Guide (Topics inCurrent Chemistry)”, edited by Norio Miyaura and S. L. Buchwald(editions Springer), or “Metal-Catalyzed Cross-Coupling Reactions”,edited by Armin de Meijere and François Diederich (editions WILEY-VCH).This is shown in Scheme 23.

Alternatively, the compounds of formula I wherein R₁, R₂, R₃, R₄, R₅,R₆, R₇, m and n are as defined above, can be obtained by transformationof another, closely related, compound of formula I (or an analoguethereof) using standard synthesis techniques known to the person skilledin the art. Non-exhaustive examples include oxidation reactions,reduction reactions, hydrolysis reactions, coupling reactions, aromaticnucleophilic or electrophilic substitution reactions, nucleophilicsubstitution reactions, nucleophilic addition reactions, andhalogenation reactions.

Certain intermediates described in the above schemes are novel and assuch form a further aspect of the invention.

The compounds of formula I can be used in the agricultural sector andrelated fields of use e.g. as active ingredients for controlling plantpests or on non-living materials for control of spoilage microorganismsor organisms potentially harmful to man. The novel compounds aredistinguished by excellent activity at low rates of application, bybeing well tolerated by plants and by being environmentally safe. Theyhave very useful curative, preventive and systemic properties and may beused for protecting numerous cultivated plants. The compounds of formulaI can be used to inhibit or destroy the pests that occur on plants orparts of plants (fruit, blossoms, leaves, stems, tubers, roots) ofdifferent crops of useful plants, while at the same time protecting alsothose parts of the plants that grow later e.g. from phytopathogenicmicroorganisms.

It is also possible to use compounds of formula I as fungicide. The term“fungicide” as used herein means a compound that controls, modifies, orprevents the growth of fungi. The term “fungicidally effective amount”means the quantity of such a compound or combination of such compoundsthat is capable of producing an effect on the growth of fungi.Controlling or modifying effects include all deviation from naturaldevelopment, such as killing, retardation and the like, and preventionincludes barrier or other defensive formation in or on a plant toprevent fungal infection.

It is also possible to use compounds of formula I as dressing agents forthe treatment of plant propagation material, e.g., seed, such as fruits,tubers or grains, or plant cuttings (for example rice), for theprotection against fungal infections as well as against phytopathogenicfungi occurring in the soil. The propagation material can be treatedwith a composition comprising a compound of formula I before planting:seed, for example, can be dressed before being sown. The compounds offormula I can also be applied to grains (coating), either byimpregnating the seeds in a liquid formulation or by coating them with asolid formulation. The composition can also be applied to the plantingsite when the propagation material is being planted, for example, to theseed furrow during sowing. The invention relates also to such methods oftreating plant propagation material and to the plant propagationmaterial so treated.

Furthermore the compounds according to present invention can be used forcontrolling fungi in related areas, for example in the protection oftechnical materials, including wood and wood related technical products,in food storage, in hygiene management.

In addition, the invention could be used to protect non-living materialsfrom fungal attack, e.g. lumber, wall boards and paint.

Compounds of formula I and fungicidal compositions containing them maybe used to control plant diseases caused by a broad spectrum of fungalplant pathogens. They are effective in controlling a broad spectrum ofplant diseases, such as foliar pathogens of ornamental, turf, vegetable,field, cereal, and fruit crops.

These fungi and fungal vectors of disease, as well as phytopathogenicbacteria and viruses, which may be controlled are for example:

Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp,Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A.niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomycesdermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp.including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea,Candida spp. including C. albicans, C. glabrata, C. krusei, C.lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans,Ceratocystis spp, Cercospora spp. including C. arachidicola,Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,

Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.musae,

Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp,Elsinoe spp,

Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E.cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F.graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F.proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis,Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum,Glomerella cingulate, Guignardia bidwellii, Gymnosporangiumjuniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasmaspp. including H. capsulatum, Laetisaria fuciformis, Leptographiumlindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochiumnivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp.including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostomapiceae, Paracoccidioides spp, Penicillium spp. including P. digitatum,P. italicum, Petriellidium spp, Peronosclerospora spp. Including P.maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaerianodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp,Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans,Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp.,Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxabetae, Pseudocercosporella herpotrichoides, Pseudomonas spp,Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatracheiphila, Puccinia Spp. including P. hordei, P. recondita, P.striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp,Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum,Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus,Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S.prolificans, Schizothyrium pomi,

Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S.tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerothecafuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp.,Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola,Tilletia spp, Trichoderma spp. including T. harzianum, T.pseudokoningii, T. viride,

Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilagospp, Venturia spp. including V. inaequalis, Verticillium spp, andXanthomonas spp.

In particular, compounds of formula I and fungicidal compositionscontaining them may be used to control plant diseases caused by a broadspectrum of fungal plant pathogens in the Basidiomycete, Ascomycete,Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete,Glomeromycete and/or Mucoromycete classes.

These pathogens may include:

Oomycetes, including Phytophthora diseases such as those caused byPhytophthora capsici, Phytophthora infestans, Phytophthora sojae,Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi,Phytophthora citricola, Phytophthora citrophthora and Phytophthoraerythroseptica; Pythium diseases such as those caused by Pythiumaphanidermaturn, Pythium arrhenomanes, Pythium graminicola, Pythiumirregulare and Pythium ultimum; diseases caused by Peronosporales suchas Peronospora destructor, Peronospora parasitica, Plasmopara viticola,Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida,Sclerophthora macrospora and Bremia lactucae; and others such asAphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghiand Sclerospora graminicola.

Ascomycetes, including blotch, spot, blast or blight diseases and/orrots for example those caused by Pleosporales such as Stemphyliumsolani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeriaturcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phomadestructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii,Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeriamaculans, Hendersonia creberrima, Helminthosporium triticirepentis,Setosphaeria turcica, Drechslera glycines, Didymella bryoniae,Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus,Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophoratritici-repentis, Alternaria alternata, Alternaria brassicicola,Alternaria solani and Alternaria tomatophila, Capnodiales such asSeptoria tritici, Septoria nodorum, Septoria glycines, Cercosporaarachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporellacapsellae and Cercosporella herpotrichoides, Cladosporium carpophilum,Cladosporium effusum, Passalora fulva, Cladosporium oxysporum,Dothistroma septosporum, Isariopsis clavispora, Mycosphaerellafijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii,Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporellaherpotrichoides, Ramularia beticola, Ramularia collo-cygni,Magnaporthales such as Gaeumannomyces graminis, Magnaporthe grisea,Pyricularia oryzae, Diaporthales such as Anisogramma anomala,Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum,Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconiumjuglandinum, Phomopsis viticola, Sirococcusclavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsaceratosperma, and others such as Actinothyrium graminis, Ascochyta pisi,Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans,Asperisporium caricae, Blumeriella jaapii, Candida spp., Capnodiumramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystisparadoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioidesspp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris,Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata,Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi,Gloeodes pomigena, Gloeosporium perennans; Gloeotinia ternulenta,Griphospaeria corticola, Kabatiella lini, Leptographium microsporum,Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssoninagraminicola, Microdochium nivale, Monilinia fructicola, Monographellaalbescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostomanovo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum,Pestalotia rhododendri, Petrieffidium spp., Pezicula spp., Phialophoragregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalosporaabdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopezizamedicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdoclinepseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporiumspp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor,Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae,Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonemaphacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata,Thielviopsis basicola, Trichoseptoria fructigena, Zygophialajamaicensis; powdery mildew diseases for example those caused byErysiphales such as Blumeria graminis, Erysiphe polygoni, Uncinulanecator, Sphaerotheca fuligena, Podosphaera leucotricha, Podospaeramacularis Golovinomyces cichoracearum, Leveillula taurica, Microsphaeradiffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis;molds for example those caused by Botryosphaeriales such as Dothiorellaaromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea,Botryotinia affii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodiatheobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllostictacucurbitacearum; anthracnoses for example those caused by Glommerelalessuch as Colletotrichum gloeosporioides, Colletotrichum lagenarium,Colletotrichum gossypii, Glomerella cingulata, and Colletotrichumgraminicola; and wilts or blights for example those caused byHypocreales such as Acremonium strictum, Claviceps purpurea, Fusariumculmorum, Fusarium graminearum, Fusarium virguliforme, Fusariumoxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp. cubense,Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladiumspp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride,Trichothecium roseum, and Verticillium theobromae.

Basidiomycetes, including smuts for example those caused byUstilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilagotritici, Ustilago zeae, rusts for example those caused by Puccinialessuch as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporiumipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata,Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei,Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis,Pucciniastrum coryli, or Uredinales such as Cronartium ribicola,Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsorapachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzscheliadiscolor and Uromyces viciae-fabae; and other rots and diseases such asthose caused by Cryptococcus spp., Exobasidium vexans, Marasmiellusinoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis,Urocystis agropyri, Itersonilia perplexans, Corticium invisum,Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani,Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora,Neovossia moliniae and Tilletia caries.

Blastocladiomycetes, such as Physoderma maydis.

Mucoromycetes, such as Choanephora cucurbitarum; Mucor spp.; Rhizopusarrhizus,

As well as diseases caused by other species and genera closely relatedto those listed above.

In addition to their fungicidal activity, the compounds and compositionscomprising them may also have activity against bacteria such as Erwiniaamylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonassyringae, Streptomyces scabies and other related species as well ascertain protozoa.

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise perennial and annual crops, such asberry plants for example blackberries, blueberries, cranberries,raspberries and strawberries; cereals for example barley, maize (corn),millet, oats, rice, rye, sorghum triticale and wheat; fibre plants forexample cotton, flax, hemp, jute and sisal; field crops for examplesugar and fodder beet, coffee, hops, mustard, oilseed rape (canola),poppy, sugar cane, sunflower, tea and tobacco; fruit trees for exampleapple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pearand plum; grasses for example Bermuda grass, bluegrass, bentgrass,centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass;herbs such as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

The useful plants and/or target crops in accordance with the inventioninclude conventional as well as genetically enhanced or engineeredvarieties such as, for example, insect resistant (e.g. Bt. and VIPvarieties) as well as disease resistant, herbicide tolerant (e.g.glyphosate- and glufosinate-resistant maize varieties commerciallyavailable under the trade names RoundupReady® and LibertyLink®) andnematode tolerant varieties. By way of example, suitable geneticallyenhanced or engineered crop varieties include the Stoneville 5599BRcotton and Stoneville 4892BR cotton varieties.

The term “useful plants” and/or “target crops” is to be understood asincluding also useful plants that have been rendered tolerant toherbicides like bromoxynil or classes of herbicides (such as, forexample, HPPD inhibitors, ALS inhibitors, for example primisulfuron,prosulfuron and trifloxysulfuron, EPSPS(5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” and/or “target crops” is to be understood asincluding those which naturally are or have been rendered resistant toharmful insects. This includes plants transformed by the use ofrecombinant DNA techniques, for example, to be capable of synthesisingone or more selectively acting toxins, such as are known, for example,from toxin-producing bacteria. Examples of toxins which can be expressedinclude δ-endotoxins, vegetative insecticidal proteins (Vip),insecticidal proteins of bacteria colonising nematodes, and toxinsproduced by scorpions, arachnids, wasps and fungi. An example of a cropthat has been modified to express the Bacillus thuringiensis toxin isthe Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprisingmore than one gene that codes for insecticidal resistance and thusexpresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seedmaterial thereof can also be resistant to multiple types of pests(so-called stacked transgenic events when created by geneticmodification). For example, a plant can have the ability to express aninsecticidal protein while at the same time being herbicide tolerant,for example Herculex I® (Dow AgroSciences, Pioneer Hi-BredInternational).

The term “useful plants” and/or “target crops” is to be understood asincluding also useful plants which have been so transformed by the useof recombinant DNA techniques that they are capable of synthesisingantipathogenic substances having a selective action, such as, forexample, the so-called “pathogenesis-related proteins” (PRPs, see e.g.EP-A-0 392 225). Examples of such antipathogenic substances andtransgenic plants capable of synthesising such antipathogenic substancesare known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353191. The methods of producing such transgenic plants are generally knownto the person skilled in the art and are described, for example, in thepublications mentioned above.

Toxins that can be expressed by transgenic plants include, for example,insecticidal proteins from Bacillus cereus or Bacillus popilliae; orinsecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins,e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, orvegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A;or insecticidal proteins of bacteria colonising nematodes, for examplePhotorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens,Xenorhabdus nematophilus; toxins produced by animals, such as scorpiontoxins, arachnid toxins, wasp toxins and other insect-specificneurotoxins; toxins produced by fungi, such as Streptomycetes toxins,plant lectins, such as pea lectins, barley lectins or snowdrop lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin, papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ionchannel blockers, such as blockers of sodium or calcium channels,juvenile hormone esterase, diuretic hormone receptors, stilbenesynthase, bibenzyl synthase, chitinases and glucanases.

Further, in the context of the present invention there are to beunderstood by δ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2,Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins(Vip), for example Vip1, Vip2, Vip3 or Vip3A, expressly also hybridtoxins, truncated toxins and modified toxins. Hybrid toxins are producedrecombinantly by a new combination of different domains of thoseproteins (see, for example, WO 02/15701). Truncated toxins, for examplea truncated Cry1Ab, are known. In the case of modified toxins, one ormore amino acids of the naturally occurring toxin are replaced. In suchamino acid replacements, preferably non-naturally present proteaserecognition sequences are inserted into the toxin, such as, for example,in the case of Cry3A055, a cathepsin-G-recognition sequence is insertedinto a Cry3A toxin (see WO03/018810).

More examples of such toxins or transgenic plants capable ofsynthesising such toxins are disclosed, for example, in EP-A-0 374 753,WO93/07278, WO95/34656, EP-A-0 427 529, EP-A-451 878 and WO03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. Cryl-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.

2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.

7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

The term “locus” as used herein means fields in or on which plants aregrowing, or where seeds of cultivated plants are sown, or where seedwill be placed into the soil. It includes soil, seeds, and seedlings, aswell as established vegetation.

The term “plants” refers to all physical parts of a plant, includingseeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, andfruits.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There may be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants may be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

Pesticidal agents referred to herein using their common name are known,for example, from “The Pesticide Manual”, 15th Ed., British CropProtection Council 2009.

The compounds of formula I may be used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation. To this end they may be conveniently formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g. for agricultural use, can be solidor liquid and are substances useful in formulation technology, e.g.natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

Suspension concentrates are aqueous formulations in which finely dividedsolid particles of the active compound are suspended. Such formulationsinclude anti-settling agents and dispersing agents and may furtherinclude a wetting agent to enhance activity as well an anti-foam and acrystal growth inhibitor. In use, these concentrates are diluted inwater and normally applied as a spray to the area to be treated. Theamount of active ingredient may range from 0.5% to 95% of theconcentrate.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other liquid carriers. The particlescontain the active ingredient retained in a solid matrix. Typical solidmatrices include fuller's earth, kaolin clays, silicas and other readilywet organic or inorganic solids. Wettable powders normally contain from5% to 95% of the active ingredient plus a small amount of wetting,dispersing or emulsifying agent.

Emulsifiable concentrates are homogeneous liquid compositionsdispersible in water or other liquid and may consist entirely of theactive compound with a liquid or solid emulsifying agent, or may alsocontain a liquid carrier, such as xylene, heavy aromatic naphthas,isophorone and other non-volatile organic solvents. In use, theseconcentrates are dispersed in water or other liquid and normally appliedas a spray to the area to be treated. The amount of active ingredientmay range from 0.5% to 95% of the concentrate.

Granular formulations include both extrudates and relatively coarseparticles and are usually applied without dilution to the area in whichtreatment is required. Typical carriers for granular formulationsinclude sand, fuller's earth, attapulgite clay, bentonite clays,montmorillonite clay, vermiculite, perlite, calcium carbonate, brick,pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corncobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate,sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide,titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth,calcium sulphate and other organic or inorganic materials which absorbor which can be coated with the active compound. Granular formulationsnormally contain 5% to 25% of active ingredients which may includesurface-active agents such as heavy aromatic naphthas, kerosene andother petroleum fractions, or vegetable oils; and/or stickers such asdextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingredient with finelydivided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the activeingredient enclosed in an inert porous shell which allows escape of theenclosed material to the surroundings at controlled rates. Encapsulateddroplets are typically 1 to 50 microns in diameter. The enclosed liquidtypically constitutes 50 to 95% of the weight of the capsule and mayinclude solvent in addition to the active compound. Encapsulatedgranules are generally porous granules with porous membranes sealing thegranule pore openings, retaining the active species in liquid forminside the granule pores. Granules typically range from 1 millimeter to1 centimeter and preferably 1 to 2 millimeters in diameter. Granules areformed by extrusion, agglomeration or prilling, or are naturallyoccurring. Examples of such materials are vermiculite, sintered clay,kaolin, attapulgite clay, sawdust and granular carbon. Shell or membranematerials include natural and synthetic rubbers, cellulosic materials,styrene-butadiene copolymers, polyacrylonitriles, polyacrylates,polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for agrochemical applications include simplesolutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurisedsprayers, wherein the active ingredient is dispersed in finely-dividedform as a result of vaporisation of a low boiling dispersant solventcarrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful informulating the compositions of the invention in the formulation typesdescribed above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water,toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethylketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone,amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol,alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine,p-diethylbenzene, diethylene glycol, diethylene glycol abietate,diethylene glycol butyl ether, diethylene glycol ethyl ether, diethyleneglycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide,1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether,dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethylacetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane,2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycolbutyl ether, ethylene glycol methyl ether, gamma-butyrolactone,glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate,hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate,isooctane, isophorone, isopropyl benzene, isopropyl myristate, lacticacid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamylketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyloleate, methylene chloride, m-xylene, n-hexane, n-octylamine,octadecanoic acid, octyl amine acetate, oleic acid, oleylamine,o-xylene, phenol, polyethylene glycol (PEG400), propionic acid,propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene,triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin,mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amylacetate, butyl acetate, methanol, ethanol, isopropanol, and highermolecular weight alcohols such as amyl alcohol, tetrahydrofurfurylalcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol,glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrierof choice for the dilution of concentrates.

Suitable solid carriers include, for example, talc, titanium dioxide,pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk,diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller'searth, cotton seed hulls, wheat flour, soybean flour, pumice, woodflour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed inboth said liquid and solid compositions, especially those designed to bediluted with carrier before application. These agents, when used,normally comprise from 0.1% to 15% by weight of the formulation. Theycan be anionic, cationic, non-ionic or polymeric in character and can beemployed as emulsifying agents, wetting agents, suspending agents or forother purposes. Typical surface active agents include salts of alkylsulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C.sub. 18 ethoxylate;alcohol-alkylene oxide addition products, such as tridecylalcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate;alkylnaphthalenesulfonate salts, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride; polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions includecrystallisation inhibitors, viscosity modifiers, suspending agents,spray droplet modifiers, pigments, antioxidants, foaming agents,anti-foaming agents, light-blocking agents, compatibilizing agents,antifoam agents, sequestering agents, neutralising agents and buffers,corrosion inhibitors, dyes, odorants, spreading agents, penetrationaids, micronutrients, emollients, lubricants and sticking agents.

In addition, further, other biocidally active ingredients orcompositions may be combined with the compositions of the invention andused in the methods of the invention and applied simultaneously orsequentially with the compositions of the invention. When appliedsimultaneously, these further active ingredients may be formulatedtogether with the compositions of the invention or mixed in, forexample, the spray tank. These further biocidally active ingredients maybe fungicides, herbicides, insecticides, bactericides, acaricides,nematicides and/or plant growth regulators.

In addition, the compositions of the invention may also be applied withone or more systemically acquired resistance inducers (“SAR” inducer).SAR inducers are known and described in, for example, U.S. Pat. No.6,919,298 and include, for example, salicylates and the commercial SARinducer acibenzolar-S-methyl.

The compounds of formula I are normally used in the form of compositionsand can be applied to the crop area or plant to be treated,simultaneously or in succession with further compounds. These furthercompounds can be e.g. fertilizers or micronutrient donors or otherpreparations, which influence the growth of plants. They can also beselective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of formula I may be used in the form of (fungicidal)compositions for controlling or protecting against phytopathogenicmicroorganisms, comprising as active ingredient at least one compound offormula I or of at least one preferred individual compound asabove-defined, in free form or in agrochemically usable salt form, andat least one of the above-mentioned adjuvants.

The invention therefore provides a composition, preferably a fungicidalcomposition, comprising at least one compound formula I anagriculturally acceptable carrier and optionally an adjuvant. Anagricultural acceptable carrier is for example a carrier that issuitable for agricultural use. Agricultural carriers are well known inthe art. Preferably said composition may comprise at least one or morepesticidally active compounds, for example an additional fungicidalactive ingredient in addition to the compound of formula I.

The compound of formula (I) may be the sole active ingredient of acomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities.

Examples of suitable additional active ingredients include the followingacycloamino acid fungicides, aliphatic nitrogen fungicides, amidefungicides, anilide fungicides, antibiotic fungicides, aromaticfungicides, arsenical fungicides, aryl phenyl ketone fungicides,benzamide fungicides, benzanilide fungicides, benzimidazole fungicides,benzothiazole fungicides, botanical fungicides, bridged diphenylfungicides, carbamate fungicides, carbanilate fungicides, conazolefungicides, copper fungicides, dicarboximide fungicides, dinitrophenolfungicides, dithiocarbamate fungicides, dithiolane fungicides, furamidefungicides, furanilide fungicides, hydrazide fungicides, imidazolefungicides, mercury fungicides, morpholine fungicides, organophosphorousfungicides, organotin fungicides, oxathiin fungicides, oxazolefungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazolefungicides, pyridine fungicides, pyrimidine fungicides, pyrrolefungicides, quaternary ammonium fungicides, quinoline fungicides,quinone fungicides, quinoxaline fungicides, strobilurin fungicides,sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides,thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,triazine fungicides, triazole fungicides, triazolopyrimidine fungicides,urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include thefollowing: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acidmethoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide,1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1),1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]amide,(5-Chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,(E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone,4-chloro-2-cyano-N, -dimethyl-5-p-tolylimidazole-1-sulfonamide,N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide,N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide,N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,(.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,2′,6′-dibromo-2-methyl-4-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,1-imidazolyl-1-(4′-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate,methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate,methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate,methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate,methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate,methyl(E),(E)-2-{2-(3-methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate,3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine),2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinylalcohol, 4-chlorophenyl-3-iodopropargyl formal,3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallylalcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyln-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinylcyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenolderivatives, such as tribromophenol, tetrachlorophenol,3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol,dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol,2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone;4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone,4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one,3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione,N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs,alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin,amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin,azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide,benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron,benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril,benzamorf, benzohydroxamic acid, berberine, bethoxazin, biloxazol,binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin-S,boscalid, bromothalonil, bromuconazole, bupirimate, buthiobate,butylamine calcium polysulfide, captafol, captan, carbamorph,carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone,CGA41396, CGA41397, chinomethionate, chitosan, chlobenthiazone,chloraniformethan, chloranil, chlorfenazole, chloroneb, chloropicrin,chlorothalonil, chlorozolinate, chlozolinate, climbazole, clotrimazole,clozylacon, copper containing compounds such as copper acetate, coppercarbonate, copper hydroxide, copper naphthenate, copper oleate, copperoxychloride, copper oxyquinolate, copper silicate, copper sulphate,copper tallate, copper zinc chromate and Bordeaux mixture, cresol,cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid,cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole,cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid,di-2-pyridyl disulphide 1,1′-dioxide, dichlofluanid, diclomezine,dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol,diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim,O,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone,dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M,dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon,diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon,dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin,dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole,etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl(Z)—N-benzyl-N ([methyl (methyl-thioethylideneamino-oxycarbonyl) amino]thio)-ß-alaninate, etridiazole, famoxadone, fenamidone, fenaminosulf,fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan,fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine,fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam,fludioxonil, flumetover, flumorph, flupicolide, fluopyram, fluoroimide,fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole,flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet,formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil,furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin,guazatine, halacrinate, hexa chlorobenzene, hexachlorobutadiene,hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen,hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate,imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb,ipconazole, iprobenfos, iprodione, iprovalicarb, isopropanyl butylcarbamate, isoprothiolane, isopyrazam, isotianil, isovaledione,izopamfos, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908,mancozeb, mandipropamid, maneb, mebenil, mecarbinzid, mefenoxam,mepanipyrim, mepronil, mercuric chloride, mercurous chloride,meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole,methasulfocarb, methfuroxam, methyl bromide, methyl iodide, methylisothiocyanate, metiram, metiram-zinc, metominostrobin, metrafenone,metsulfovax, milneb, moroxydine, myclobutanil, myclozolin, nabam,natamycin, neoasozin, nickel dimethyldithiocarbamate, nitrostyrene,nitrothal-iso-propyl, nuarimol, octhilinone, ofurace, organomercurycompounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxine-copper,oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate,penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad,phenamacril, phenazin oxide, phosdiphen, phosetyl-AI, phosphorus acids,phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D,polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine,propamocarb, propiconazole, propineb, propionic acid, proquinazid,prothiocarb, prothioconazole, pyracarbolid, pyraclostrobin,pyrametrostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril,pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyroxychlor,pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinacetol,quinazamid, quinconazole, quinomethionate, quinoxyfen, quintozene,rabenzazole, santonin, sedaxane, silthiofam, simeconazole, sipconazole,sodium pentachlorophenate, solatenol, spiroxamine, streptomycin,sulphur, sultropen, tebuconazole, tebfloquin, tecloftalam, tecnazene,tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen,thifluzamide, 2-(thiocyanomethylthio) benzothiazole, thiophanate-methyl,thioquinox, thiram, tiadinil, timibenconazole, tioxymid,tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triamiphos,triarimol, triazbutil, triazoxide, tricyclazole, tridemorph,trifloxystrobin, triflumazole, triforine, triflumizole, triticonazole,uniconazole, urbacide, validamycin, valifenalate, vapam, vinclozolin,zarilamid, zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. No. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO-9615121 and also withanthelmintic active cyclic depsipeptides such as those described inWO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334,EP-382173, and EP-503538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO95/19363 or WO04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos,chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl,demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos,dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate,isoxathion, malathion, methacriphos, methamidophos, methidathion,methyl-parathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate,phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate,phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

The following mixtures of the compounds of formula I with activeingredients are preferred (the abbreviation “TX” means “one compoundselected from the group consisting of the compounds described in A1 toA18 (above) of the present invention”):

an adjuvant selected from the group of substances consisting ofpetroleum oils (alternative name) (628)+TX,

an acaricide selected from the group of substances consisting of1,1-bis(4-chloro-phenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts name)(1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC name)(1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name) (981)+TX,abamectin (1)+TX, acequinocyl (3)+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, alpha-cypermethrin(202)+TX, amidithion (870)+TX, amidoflumet [CCN]+TX, amidothioate(872)+TX, amiton (875)+TX, amiton hydrogen oxalate (875)+TX, amitraz(24)+TX, aramite (881)+TX, arsenous oxide (882)+TX, AVI 382 (compoundcode)+TX, AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX, azocyclotin(46)+TX, azothoate (889)+TX, benomyl (62)+TX, benoxafos (alternativename) [CCN]+TX, benzoximate (71)+TX, benzyl benzoate (IUPAC name)[CCN]+TX, bifenazate (74)+TX, bifenthrin (76)+TX, binapacryl (907)+TX,brofenvalerate (alternative name)+TX, bromo-cyclen (918)+TX, bromophos(920)+TX, bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin(99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX, butylpyridaben(alternative name)+TX, calcium polysulfide (IUPAC name) (111)+TX,camphechlor (941)+TX, carbanolate (943)+TX, carbaryl (115)+TX,carbofuran (118)+TX, carbophenothion (947)+TX, CGA 50′439 (developmentcode) (125)+TX, chinomethionat (126)+TX, chlorbenside (959)+TX,chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorfenapyr (130)+TX, chlorfenethol (968)+TX, chlorfenson (970)+TX,chlorfensulfide (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate(975)+TX, chloromebuform (977)+TX, chloromethiuron (978)+TX,chloropropylate (983)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl(146)+TX, chlorthiophos (994)+TX, cinerin I (696)+TX, cinerin II(696)+TX, cinerins (696)+TX, clofentezine (158)+TX, closantel(alternative name) [CCN]+TX, coumaphos (174)+TX, crotamiton (alternativename) [CCN]+TX, crotoxyphos (1010)+TX, cufraneb (1013)+TX, cyanthoate(1020)+TX, cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin(196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM (1032)+TX, DDT(219)+TX, demephion (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O(1038)+TX, demeton-O-methyl (224)+TX, demeton-S (1038)+TX,demeton-S-methyl (224)+TX, demeton-S-methylsulfon (1039)+TX,diafenthiuron (226)+TX, dialifos (1042)+TX, diazinon (227)+TX,dichlofluanid (230)+TX, dichlorvos (236)+TX, dicliphos (alternativename)+TX, dicofol (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX,dimefox (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)(653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton(269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6 [CCN]+TX,dinocton (1090)+TX, dinopenton (1092)+TX, dinosulfon (1097)+TX,dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl sulfone (IUPACname) (1103)+TX, disulfiram (alternative name) [CCN]+TX, disulfoton(278)+TX, DNOC (282)+TX, dofenapyn (1113)+TX, doramectin (alternativename) [CCN]+TX, endosulfan (294)+TX, endothion (1121)+TX, EPN (297)+TX,eprinomectin (alternative name) [CCN]+TX, ethion (309)+TX,ethoate-methyl (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX,fenazaflor (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad (alternativename)+TX, fenpyroximate (345)+TX, fenson (1157)+TX, fentrifanil(1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX, fluacrypyrim(360)+TX, fluazuron (1166)+TX, flubenzimine (1167)+TX, flucycloxuron(366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX, flufenoxuron(370)+TX, flumethrin (372)+TX, fluorbenside (1174)+TX, fluvalinate(1184)+TX, FMC 1137 (development code) (1185)+TX, formetanate (405)+TX,formetanate hydrochloride (405)+TX, formothion (1192)+TX, formparanate(1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox (424)+TX,heptenophos (432)+TX, hexadecyl cyclopropanecarboxylate (IUPAC/ChemicalAbstracts name) (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPACname) (542)+TX, isocarbophos (alternative name) (473)+TX, isopropylO-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX, jasmolin II(696)+TX, jodfenphos (1248)+TX, lindane (430)+TX, lufenuron (490)+TX,malathion (492)+TX, malonoben (1254)+TX, mecarbam (502)+TX, mephosfolan(1261)+TX, mesulfen (alternative name) [CCN]+TX, methacrifos (1266)+TX,methamidophos (527)+TX, methidathion (529)+TX, methiocarb (530)+TX,methomyl (531)+TX, methyl bromide (537)+TX, metolcarb (550)+TX,mevinphos (556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX,milbemycin oxime (alternative name) [CCN]+TX, mipafox (1293)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512(compound code)+TX, nifluridide (1309)+TX, nikkomycins (alternativename) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloridecomplex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250 (compoundcode)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydeprofos (1324)+TX,oxydisulfoton (1325)+TX, pp′-DDT (219)+TX, parathion (615)+TX,permethrin (626)+TX, petroleum oils (alternative name) (628)+TX,phenkapton (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon (639)+TX,phoxim (642)+TX, pirimiphos-methyl (652)+TX, polychloroterpenes(traditional name) (1347)+TX, polynactins (alternative name) (653)+TX,proclonol (1350)+TX, profenofos (662)+TX, promacyl (1354)+TX, propargite(671)+TX, propetamphos (673)+TX, propoxur (678)+TX, prothidathion(1360)+TX, prothoate (1362)+TX, pyrethrin I (696)+TX, pyrethrin II(696)+TX, pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos(711)+TX, quintiofos (1381)+TX, R-1492 (development code) (1382)+TX,RA-17 (development code) (1383)+TX, rotenone (722)+TX, schradan(1389)+TX, sebufos (alternative name)+TX, selamectin (alternative name)[CCN]+TX, SI-0009 (compound code)+TX, sophamide (1402)+TX, spirodiclofen(738)+TX, spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX, sulfotep(753)+TX, sulfur (754)+TX, SZI-121 (development code) (757)+TX,tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP (1417)+TX, terbam(alternative name)+TX, tetrachlorvinphos (777)+TX, tetradifon (786)+TX,tetranactin (alternative name) (653)+TX, tetrasul (1425)+TX, thiafenox(alternative name)+TX, thiocarboxime (1431)+TX, thiofanox (800)+TX,thiometon (801)+TX, thioquinox (1436)+TX, thuringiensin (alternativename) [CCN]+TX, triamiphos (1441)+TX, triarathene (1443)+TX, triazophos(820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,trifenofos (1455)+TX, trinactin (alternative name) (653)+TX, vamidothion(847)+TX, vaniliprole [CCN] and YI-5302 (compound code)+TX,

an algicide selected from the group of substances consisting ofbethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX, coppersulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX, dichlorophen(232)+TX, endothal (295)+TX, fentin (347)+TX, hydrated lime [CCN]+TX,nabam (566)+TX, quinoclamine (714)+TX, quinonamid (1379)+TX, simazine(730)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltinhydroxide (IUPAC name) (347)+TX,

an anthelmintic selected from the group of substances consisting ofabamectin (1)+TX, crufomate (1011)+TX, doramectin (alternative name)[CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin(alternative name) [CCN]+TX, ivermectin (alternative name) [CCN]+TX,milbemycin oxime (alternative name) [CCN]+TX, moxidectin (alternativename) [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)[CCN]+TX, spinosad (737) and thiophanate (1435)+TX,

an avicide selected from the group of substances consisting ofchloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,

a bactericide selected from the group of substances consisting of1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX, copperdioctanoate (IUPAC name) (170)+TX, copper hydroxide (IUPAC name)(169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX, dipyrithione(1105)+TX, dodicin (1112)+TX, fenaminosulf (1144)+TX, formaldehyde(404)+TX, hydrargaphen (alternative name) [CCN]+TX, kasugamycin(483)+TX, kasugamycin hydrochloride hydrate (483)+TX, nickelbis(dimethyldithiocarbamate) (IUPAC name) (1308)+TX, nitrapyrin(580)+TX, octhilinone (590)+TX, oxolinic acid (606)+TX, oxytetracycline(611)+TX, potassium hydroxyquinoline sulfate (446)+TX, probenazole(658)+TX, streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,tecloftalam (766)+TX, and thiomersal (alternative name) [CCN]+TX,

a biological agent selected from the group of substances consisting ofAdoxophyes orana GV (alternative name) (12)+TX, Agrobacteriumradiobacter (alternative name) (13)+TX, Amblyseius spp. (alternativename) (19)+TX, Anagrapha falcifera NPV (alternative name) (28)+TX,Anagrus atomus (alternative name) (29)+TX, Aphelinus abdominalis(alternative name) (33)+TX, Aphidius colemani (alternative name)(34)+TX, Aphidoletes aphidimyza (alternative name) (35)+TX, Autographacalifornica NPV (alternative name) (38)+TX, Bacillus firmus (alternativename) (48)+TX, Bacillus sphaericus Neide (scientific name) (49)+TX,Bacillus thuringiensis Berliner (scientific name) (51)+TX, Bacillusthuringiensis subsp. aizawai (scientific name) (51)+TX, Bacillusthuringiensis subsp. israelensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. japonensis (scientific name) (51)+TX, Bacillusthuringiensis subsp. kurstaki (scientific name) (51)+TX, Bacillusthuringiensis subsp. tenebrionis (scientific name) (51)+TX, Beauveriabassiana (alternative name) (53)+TX, Beauveria brongniartii (alternativename) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia pomonellaGV (alternative name) (191)+TX, Dacnusa sibirica (alternative name)(212)+TX, Diglyphus isaea (alternative name) (254)+TX, Encarsia formosa(scientific name) (293)+TX, Eretmocerus eremicus (alternative name)(300)+TX, Helicoverpa zea NPV (alternative name) (431)+TX,Heterorhabditis bacteriophora and H. megidis (alternative name)(433)+TX, Hippodamia convergens (alternative name) (442)+TX, Leptomastixdactylopii (alternative name) (488)+TX, Macrolophus caliginosus(alternative name) (491)+TX, Mamestra brassicae NPV (alternative name)(494)+TX, Metaphycus helvolus (alternative name) (522)+TX, Metarhiziumanisopliae var. acridum (scientific name) (523)+TX, Metarhiziumanisopliae var. anisopliae (scientific name) (523)+TX, Neodiprionsertifer NPV and N. lecontei NPV (alternative name) (575)+TX, Orius spp.(alternative name) (596)+TX, Paecilomyces fumosoroseus (alternativename) (613)+TX, Phytoseiulus persimilis (alternative name) (644)+TX,Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientificname) (741)+TX, Steinernema bibionis (alternative name) (742)+TX,Steinernema carpocapsae (alternative name) (742)+TX, Steinernema feltiae(alternative name) (742)+TX, Steinernema glaseri (alternative name)(742)+TX, Steinernema riobrave (alternative name) (742)+TX, Steinernemariobravis (alternative name) (742)+TX, Steinernema scapterisci(alternative name) (742)+TX, Steinernema spp. (alternative name)(742)+TX, Trichogramma spp. (alternative name) (826)+TX, Typhlodromusoccidentalis (alternative name) (844) and Verticillium lecanii(alternative name) (848)+TX,

a soil sterilant selected from the group of substances consisting ofiodomethane (IUPAC name) (542) and methyl bromide (537)+TX,

a chemosterilant selected from the group of substances consisting ofapholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan(alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatif(alternative name) [CCN]+TX, hemel [CCN]+TX, hempa [CCN]+TX, metepa[CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, morzid[CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX,thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name)[CCN]+TX, tretamine (alternative name) [CCN] and uredepa (alternativename) [CCN]+TX,

an insect pheromone selected from the group of substances consisting of(E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (IUPAC name) (222)+TX,(E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX,(E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,(E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,(Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadec-11-enal(IUPAC name) (436)+TX, (Z)-hexadec-11-en-1-yl acetate (IUPAC name)(437)+TX, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,(Z)-icos-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-al(IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,(Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,(7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,(9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,(9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol with4-methylnonan-5-one (IUPAC name) (544)+TX, alpha-multistriatin(alternative name) [CCN]+TX, brevicomin (alternative name) [CCN]+TX,codlelure (alternative name) [CCN]+TX, codlemone (alternative name)(167)+TX, cuelure (alternative name) (179)+TX, disparlure (277)+TX,dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate(IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate (IUPAC name)(284)+TX, dominicalure (alternative name) [CCN]+TX, ethyl4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alternative name)[CCN]+TX, frontalin (alternative name) [CCN]+TX, gossyplure (alternativename) (420)+TX, grandlure (421)+TX, grandlure I (alternative name)(421)+TX, grandlure II (alternative name) (421)+TX, grandlure III(alternative name) (421)+TX, grandlure IV (alternative name) (421)+TX,hexalure [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol(alternative name) [CCN]+TX, japonilure (alternative name) (481)+TX,lineatin (alternative name) [CCN]+TX, litlure (alternative name)[CCN]+TX, looplure (alternative name) [CCN]+TX, medlure [CCN]+TX,megatomoic acid (alternative name) [CCN]+TX, methyl eugenol (alternativename) (540)+TX, muscalure (563)+TX, octadeca-2,13-dien-1-yl acetate(IUPAC name) (588)+TX, octadeca-3,13-dien-1-yl acetate (IUPAC name)(589)+TX, orfralure (alternative name) [CCN]+TX, oryctalure (alternativename) (317)+TX, ostramone (alternative name) [CCN]+TX, siglure [CCN]+TX,sordidin (alternative name) (736)+TX, sulcatol (alternative name)[CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, trimedlure(839)+TX, trimedlure A (alternative name) (839)+TX, trimedlure B₁(alternative name) (839)+TX, trimedlure B₂ (alternative name) (839)+TX,trimedlure C (alternative name) (839) and trunc-call (alternative name)[CCN]+TX,

an insect repellent selected from the group of substances consisting of2-(octylthio)-ethanol (IUPAC name) (591)+TX, butopyronoxyl (933)+TX,butoxy(polypropylene glycol) (936)+TX, dibutyl adipate (IUPAC name)(1046)+TX, dibutyl phthalate (1047)+TX, dibutyl succinate (IUPAC name)(1048)+TX, diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX,dimethyl phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide[CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide [CCN]+TX,oxamate [CCN] and picaridin [CCN]+TX,

an insecticide selected from the group of substances consisting of1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name) (1058)+TX,1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC name) (1056), +TX,1,2-dichloropropane (IUPAC/Chemical Abstracts name) (1062)+TX,1,2-dichloropropane with 1,3-dichloropropene (IUPAC name) (1063)+TX,1-bromo-2-chloroethane (IUPAC/Chemical Abstracts name) (916)+TX,2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)(1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate(IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate(IUPAC/Chemical Abstracts name) (1109)+TX, 2-(2-butoxyethoxy)ethylthiocyanate (IUPAC/Chemical Abstracts name) (935)+TX,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate (IUPAC/ChemicalAbstracts name) (1084)+TX, 2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name)(986)+TX, 2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,2-imidazolidone (IUPAC name) (1225)+TX, 2-isovalerylindan-1,3-dione(IUPAC name) (1246)+TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate(IUPAC name) (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name)(1433)+TX, 3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name) (1283)+TX,4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate (IUPAC name)(1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate (IUPACname) (1085)+TX, abamectin (1)+TX, acephate (2)+TX, acetamiprid (4)+TX,acethion (alternative name) [CCN]+TX, acetoprole [CCN]+TX, acrinathrin(9)+TX, acrylonitrile (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name) [CCN]+TX,aluminium phosphide (640)+TX, amidithion (870)+TX, amidothioate(872)+TX, aminocarb (873)+TX, amiton (875)+TX, amiton hydrogen oxalate(875)+TX, amitraz (24)+TX, anabasine (877)+TX, athidathion (883)+TX, AVI382 (compound code)+TX, AZ 60541 (compound code)+TX, azadirachtin(alternative name) (41)+TX, azamethiphos (42)+TX, azinphos-ethyl(44)+TX, azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillusthuringiensis delta endotoxins (alternative name) (52)+TX, bariumhexafluorosilicate (alternative name) [CCN]+TX, barium polysulfide(IUPAC/Chemical Abstracts name) (892)+TX, barthrin [CCN]+TX, Bayer22/190 (development code) (893)+TX, Bayer 22408 (development code)(894)+TX, bendiocarb (58)+TX, benfuracarb (60)+TX, bensultap (66)+TX,beta-cyfluthrin (194)+TX, beta-cypermethrin (203)+TX, bifenthrin(76)+TX, bioallethrin (78)+TX, bioallethrin S-cyclopentenyl isomer(alternative name) (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin(908)+TX, bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name)(909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate(alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen (918)+TX,bromo-DDT (alternative name) [CCN]+TX, bromophos (920)+TX,bromophos-ethyl (921)+TX, bufencarb (924)+TX, buprofezin (99)+TX,butacarb (926)+TX, butathiofos (927)+TX, butocarboxim (103)+TX, butonate(932)+TX, butoxycarboxim (104)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX, carbondisulfide (IUPAC/Chemical Abstracts name) (945)+TX, carbon tetrachloride(IUPAC name) (946)+TX, carbophenothion (947)+TX, carbosulfan (119)+TX,cartap (123)+TX, cartap hydrochloride (123)+TX, cevadine (alternativename) (725)+TX, chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone(963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride (964)+TX,chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX, chlorfenvinphos(131)+TX, chlorfluazuron (132)+TX, chlormephos (136)+TX, chloroform[CCN]+TX, chloropicrin (141)+TX, chlorphoxim (989)+TX, chlorprazophos(990)+TX, chlorpyrifos (145)+TX, chlorpyrifos-methyl (146)+TX,chlorthiophos (994)+TX, chromafenozide (150)+TX, cinerin I (696)+TX,cinerin II (696)+TX, cinerins (696)+TX, cis-resmethrin (alternativename)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper arsenate[CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX, coumithoate(1006)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos(1010)+TX, crufomate (1011)+TX, cryolite (alternative name) (177)+TX, CS708 (development code) (1012)+TX, cyanofenphos (1019)+TX, cyanophos(184)+TX, cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin(188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX, cypermethrin(201)+TX, cyphenothrin (206)+TX, cyromazine (209)+TX, cythioate(alternative name) [CCN]+TX, d-limonene (alternative name) [CCN]+TX,d-tetramethrin (alternative name) (788)+TX, DAEP (1031)+TX, dazomet(216)+TX, DDT (219)+TX, decarbofuran (1034)+TX, deltamethrin (223)+TX,demephion (1037)+TX, demephion-O (1037)+TX, demephion-S (1037)+TX,demeton (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl(224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron (226)+TX,dialifos (1042)+TX, diamidafos (1044)+TX, diazinon (227)+TX, dicapthon(1050)+TX, dichlofenthion (1051)+TX, dichlorvos (236)+TX, dicliphos(alternative name)+TX, dicresyl (alternative name) [CCN]+TX, dicrotophos(243)+TX, dicyclanil (244)+TX, dieldrin (1070)+TX, diethyl5-methylpyrazol-3-yl phosphate (IUPAC name) (1076)+TX, diflubenzuron(250)+TX, dilor (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX,dimefox (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin(1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex(1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX, dinosam(1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX, diofenolan(1099)+TX, dioxabenzofos (1100)+TX, dioxacarb (1101)+TX, dioxathion(1102)+TX, disulfoton (278)+TX, dithicrofos (1108)+TX, DNOC (282)+TX,doramectin (alternative name) [CCN]+TX, DSP (1115)+TX, ecdysterone(alternative name) [CCN]+TX, EI 1642 (development code) (1118)+TX,emamectin (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX, endrin(1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane (1124)+TX,eprinomectin (alternative name) [CCN]+TX, esfenvalerate (302)+TX,etaphos (alternative name) [CCN]+TX, ethiofencarb (308)+TX, ethion(309)+TX, ethiprole (310)+TX, ethoate-methyl (1134)+TX, ethoprophos(312)+TX, ethyl formate (IUPAC name) [CCN]+TX, ethyl-DDD (alternativename) (1056)+TX, ethylene dibromide (316)+TX, ethylene dichloride(chemical name) (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos(326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX, fenethacarb(1149)+TX, fenfluthrin (1150)+TX, fenitrothion (335)+TX, fenobucarb(336)+TX, fenoxacrim (1153)+TX, fenoxycarb (340)+TX, fenpirithrin(1155)+TX, fenpropathrin (342)+TX, fenpyrad (alternative name)+TX,fensulfothion (1158)+TX, fenthion (346)+TX, fenthion-ethyl [CCN]+TX,fenvalerate (349)+TX, fipronil (354)+TX, flonicamid (358)+TX,flubendiamide (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil (1169)+TX,flufenerim [CCN]+TX, flufenoxuron (370)+TX, flufenprox (1171)+TX,flumethrin (372)+TX, fluvalinate (1184)+TX, FMC 1137 (development code)(1185)+TX, fonofos (1191)+TX, formetanate (405)+TX, formetanatehydrochloride (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate (408)+TX,fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin (1200)+TX,gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX, guazatine (422)+TX,guazatine acetates (422)+TX, GY-81 (development code) (423)+TX,halfenprox (424)+TX, halofenozide (425)+TX, HCH (430)+TX, HEOD(1070)+TX, heptachlor (1211)+TX, heptenophos (432)+TX, heterophos[CCN]+TX, hexaflumuron (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX,hydrogen cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb (465)+TX,iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX, isazofos (1231)+TX,isobenzan (1232)+TX, isocarbophos (alternative name) (473)+TX, isodrin(1235)+TX, isofenphos (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX,isopropyl O-(methoxy-aminothiophosphoryl)salicylate (IUPAC name)(473)+TX, isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion(480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I (696)+TX,jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile hormone I(alternative name) [CCN]+TX, juvenile hormone II (alternative name)[CCN]+TX, juvenile hormone III (alternative name) [CCN]+TX, kelevan(1249)+TX, kinoprene (484)+TX, lambda-cyhalothrin (198)+TX, leadarsenate [CCN]+TX, lepimectin (CCN)+TX, leptophos (1250)+TX, lindane(430)+TX, lirimfos (1251)+TX, lufenuron (490)+TX, lythidathion(1253)+TX, m-cumenyl methylcarbamate (IUPAC name) (1014)+TX, magnesiumphosphide (IUPAC name) (640)+TX, malathion (492)+TX, malonoben(1254)+TX, mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride (513)+TX,mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam (519)+TX,metam-potassium (alternative name) (519)+TX, metam-sodium (519)+TX,methacrifos (1266)+TX, methamidophos (527)+TX, methanesulfonyl fluoride(IUPAC/Chemical Abstracts name) (1268)+TX, methidathion (529)+TX,methiocarb (530)+TX, methocrotophos (1273)+TX, methomyl (531)+TX,methoprene (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternativename) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX, methylbromide (537)+TX, methyl isothiocyanate (543)+TX, methylchloroform(alternative name) [CCN]+TX, methylene chloride [CCN]+TX, metofluthrin[CCN]+TX, metolcarb (550)+TX, metoxadiazone (1288)+TX, mevinphos(556)+TX, mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime(alternative name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin (alternativename) [CCN]+TX, naftalofos (alternative name) [CCN]+TX, naled (567)+TX,naphthalene (IUPAC/Chemical Abstracts name) (1303)+TX, NC-170(development code) (1306)+TX, NC-184 (compound code)+TX, nicotine(578)+TX, nicotine sulfate (578)+TX, nifluridide (1309)+TX, nitenpyram(579)+TX, nithiazine (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1zinc chloride complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250(compound code)+TX, nornicotine (traditional name) (1319)+TX, novaluron(585)+TX, noviflumuron (586)+TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate (IUPAC name) (1057)+TX, O,O-diethylO-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate (IUPAC name)(1074)+TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate (IUPAC name) (1075)+TX, O,O,O′,O′-tetrapropyldithiopyrophosphate (IUPAC name) (1424)+TX, oleic acid (IUPAC name)(593)+TX, omethoate (594)+TX, oxamyl (602)+TX, oxydemeton-methyl(609)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT(219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,parathion-methyl (616)+TX, penfluron (alternative name) [CCN]+TX,pentachlorophenol (623)+TX, pentachlorophenyl laurate (IUPAC name)(623)+TX, permethrin (626)+TX, petroleum oils (alternative name)(628)+TX, PH 60-38 (development code) (1328)+TX, phenkapton (1330)+TX,phenothrin (630)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone(637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX,phosphamidon (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb (651)+TX,pirimiphos-ethyl (1345)+TX, pirimiphos-methyl (652)+TX,polychlorodicyclopentadiene isomers (IUPAC name) (1346)+TX,polychloroterpenes (traditional name) (1347)+TX, potassium arsenite[CCN]+TX, potassium thiocyanate [CCN]+TX, prallethrin (655)+TX,precocene I (alternative name) [CCN]+TX, precocene II (alternative name)[CCN]+TX, precocene Ill (alternative name) [CCN]+TX, primidophos(1349)+TX, profenofos (662)+TX, profluthrin [CCN]+TX, promacyl(1354)+TX, promecarb (1355)+TX, propaphos (1356)+TX, propetamphos(673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothiofos(686)+TX, prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine(688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin(1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX, pyrethrins(696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX, pyridaphenthion(701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, pyriproxyfen(708)+TX, quassia (alternative name) [CCN]+TX, quinalphos (711)+TX,quinalphos-methyl (1376)+TX, quinothion (1380)+TX, quintiofos (1381)+TX,R-1492 (development code) (1382)+TX, rafoxanide (alternative name)[CCN]+TX, resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (developmentcode) (723)+TX, RU 25475 (development code) (1386)+TX, ryania(alternative name) (1387)+TX, ryanodine (traditional name) (1387)+TX,sabadilla (alternative name) (725)+TX, schradan (1389)+TX, sebufos(alternative name)+TX, selamectin (alternative name) [CCN]+TX, SI-0009(compound code)+TX, SI-0205 (compound code)+TX, SI-0404 (compoundcode)+TX, SI-0405 (compound code)+TX, silafluofen (728)+TX, SN 72129(development code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide(444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name) (1399)+TX,sodium hexafluorosilicate (1400)+TX, sodium pentachlorophenoxide(623)+TX, sodium selenate (IUPAC name) (1401)+TX, sodium thiocyanate[CCN]+TX, sophamide (1402)+TX, spinosad (737)+TX, spiromesifen (739)+TX,spirotetrmat (CCN)+TX, sulcofuron (746)+TX, sulcofuron-sodium (746)+TX,sulfluramid (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos (764)+TX,teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos (770)+TX, TEPP(1417)+TX, terallethrin (1418)+TX, terbam (alternative name)+TX,terbufos (773)+TX, tetrachloroethane [CCN]+TX, tetrachlorvinphos(777)+TX, tetramethrin (787)+TX, theta-cypermethrin (204)+TX,thiacloprid (791)+TX, thiafenox (alternative name)+TX, thiamethoxam(792)+TX, thicrofos (1428)+TX, thiocarboxime (1431)+TX, thiocyclam(798)+TX, thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX, thiosultap(803)+TX, thiosultap-sodium (803)+TX, thuringiensin (alternative name)[CCN]+TX, tolfenpyrad (809)+TX, tralomethrin (812)+TX, transfluthrin(813)+TX, transpermethrin (1440)+TX, triamiphos (1441)+TX, triazamate(818)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,trichlorfon (824)+TX, trichlormetaphos-3 (alternative name) [CCN]+TX,trichloronat (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX, veratrine(alternative name) (725)+TX, XMC (853)+TX, xylylcarb (854)+TX, YI-5302(compound code)+TX, zeta-cypermethrin (205)+TX, zetamethrin (alternativename)+TX, zinc phosphide (640)+TX, zolaprofos (1469) and ZXI 8901(development code) (858)+TX, cyantraniliprole [736994-63-19+TX,chlorantraniliprole [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX,cyflumetofen [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX,spinetoram [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX, meperfluthrin[915288-13-0]+TX, tetramethylfluthrin [84937-88-2]+TX, triflumezopyrim(disclosed in WO 2012/092115)+TX,

a molluscicide selected from the group of substances consisting ofbis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX,calcium arsenate [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite[CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate(IUPAC name) (352)+TX, metaldehyde (518)+TX, methiocarb (530)+TX,niclosamide (576)+TX, niclosamide-olamine (576)+TX, pentachlorophenol(623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX,thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) andtriphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole[394730-71-3]+TX,

a nematicide selected from the group of substances consisting ofAKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane (IUPAC/ChemicalAbstracts name) (1045)+TX, 1,2-dichloropropane (IUPAC/Chemical Abstractsname) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene (IUPACname) (1063)+TX, 1,3-dichloropropene (233)+TX,3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC/Chemical Abstractsname) (1065)+TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name)(980)+TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPACname) (1286)+TX, 6-isopentenylaminopurine (alternative name) (210)+TX,abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb (15)+TX, aldicarb(16)+TX, aldoxycarb (863)+TX, AZ 60541 (compound code)+TX, benclothiaz[CCN]+TX, benomyl (62)+TX, butylpyridaben (alternative name)+TX,cadusafos (109)+TX, carbofuran (118)+TX, carbon disulfide (945)+TX,carbosulfan (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX, dazomet(216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos (1044)+TX,dichlofenthion (1051)+TX, dicliphos (alternative name)+TX, dimethoate(262)+TX, doramectin (alternative name) [CCN]+TX, emamectin (291)+TX,emamectin benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,ethoprophos (312)+TX, ethylene dibromide (316)+TX, fenamiphos (326)+TX,fenpyrad (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate(408)+TX, fosthietan (1196)+TX, furfural (alternative name) [CCN]+TX,GY-81 (development code) (423)+TX, heterophos [CCN]+TX, iodomethane(IUPAC name) (542)+TX, isamidofos (1230)+TX, isazofos (1231)+TX,ivermectin (alternative name) [CCN]+TX, kinetin (alternative name)(210)+TX, mecarphon (1258)+TX, metam (519)+TX, metam-potassium(alternative name) (519)+TX, metam-sodium (519)+TX, methyl bromide(537)+TX, methyl isothiocyanate (543)+TX, milbemycin oxime (alternativename) [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrotheciumverrucaria composition (alternative name) (565)+TX, NC-184 (compoundcode)+TX, oxamyl (602)+TX, phorate (636)+TX, phosphamidon (639)+TX,phosphocarb [CCN]+TX, sebufos (alternative name)+TX, selamectin(alternative name) [CCN]+TX, spinosad (737)+TX, terbam (alternativename)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC/ChemicalAbstracts name) (1422)+TX, thiafenox (alternative name)+TX, thionazin(1434)+TX, triazophos (820)+TX, triazuron (alternative name)+TX,xylenols [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)(210)+TX, fluensulfone [318290-98-1]+TX,

a nitrification inhibitor selected from the group of substancesconsisting of potassium ethylxanthate [CCN] and nitrapyrin (580)+TX,

a plant activator selected from the group of substances consisting ofacibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX, probenazole (658) andReynoutria sachalinensis extract (alternative name) (720)+TX,

a rodenticide selected from the group of substances consisting of2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748)+TX,alpha-chlorohydrin [CCN]+TX, aluminium phosphide (640)+TX, antu(880)+TX, arsenous oxide (882)+TX, barium carbonate (891)+TX,bisthiosemi (912)+TX, brodifacoum (89)+TX, bromadiolone (91)+TX,bromethalin (92)+TX, calcium cyanide (444)+TX, chloralose (127)+TX,chlorophacinone (140)+TX, cholecalciferol (alternative name) (850)+TX,coumachlor (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen (357)+TX,fluoroacetamide (379)+TX, flupropadine (1183)+TX, flupropadinehydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH (430)+TX, hydrogencyanide (444)+TX, iodomethane (IUPAC name) (542)+TX, lindane (430)+TX,magnesium phosphide (IUPAC name) (640)+TX, methyl bromide (537)+TX,norbormide (1318)+TX, phosacetim (1336)+TX, phosphine (IUPAC name)(640)+TX, phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite[CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium arsenite[CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate (735)+TX,strychnine (745)+TX, thallium sulfate [CCN]+TX, warfarin (851) and zincphosphide (640)+TX,

a synergist selected from the group of substances consisting of2-(2-butoxyethoxy)-ethyl piperonylate (IUPAC name) (934)+TX,5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903)+TX,farnesol with nerolidol (alternative name) (324)+TX, MB-599 (developmentcode) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide(649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (developmentcode) (724)+TX, sesamex (1393)+TX, sesasmolin (1394) and sulfoxide(1406)+TX,

an animal repellent selected from the group of substances consisting ofanthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX,copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene(chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetates(422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX,thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram(856)+TX,

a virucide selected from the group of substances consisting of imanin(alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX,

a wound protectant selected from the group of substances consisting ofmercuric oxide (512)+TX, octhilinone (590) and thiophanate-methyl(802)+TX,

and biologically active compounds selected from the group consisting ofazaconazole (60207-31-0]+TX, bitertanol [70585-36-3]+TX, bromuconazole[116255-48-2]+TX, cyproconazole [94361-06-5]+TX, difenoconazole[119446-68-3]+TX, diniconazole [83657-24-3]+TX, epoxiconazole[106325-08-0]+TX, fenbuconazole [114369-43-6]+TX, fluquinconazole[136426-54-5]+TX, flusilazole [85509-19-9]+TX, flutriafol[76674-21-0]+TX, hexaconazole [79983-71-4]+TX, imazalil [35554-44-0]+TX,imibenconazole [86598-92-7]+TX, ipconazole [125225-28-7]+TX, metconazole[125116-23-6]+TX, myclobutanil [88671-89-0]+TX, pefurazoate[101903-30-4]+TX, penconazole [66246-88-6]+TX, prothioconazole[178928-70-6]+TX, pyrifenox [88283-41-4]+TX, prochloraz [67747-09-5]+TX,propiconazole [60207-90-1]+TX, simeconazole [149508-90-7]+TX,tebuconazole [107534-96-3]+TX, tetraconazole [112281-77-3]+TX,triadimefon [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole[99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol[12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol [63284-71-9]+TX,bupirimate [41483-43-6]+TX, dimethirimol [5221-53-4]+TX, ethirimol[23947-60-6]+TX, dodemorph [1593-77-7]+TX, fenpropidine [67306-00-7]+TX,fenpropimorph [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph[81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim[110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil[74738-17-3]+TX, fludioxonil [131341-86-1]+TX, benalaxyl[71626-11-4]+TX, furalaxyl [57646-30-7]+TX, metalaxyl [57837-19-1]+TX,R-metalaxyl [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl[77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim [10605-21-7]+TX,debacarb [62732-91-6]+TX, fuberidazole [3878-19-1]+TX, thiabendazole[148-79-8]+TX, chlozolinate [84332-86-5]+TX, dichlozoline[24201-58-9]+TX, iprodione [36734-19-7]+TX, myclozoline [54864-61-8]+TX,procymidone [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid[188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram [24691-80-3]+TX,flutolanil [66332-96-5]+TX, mepronil [55814-41-0]+TX, oxycarboxin[5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide[130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3][112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX, azoxystrobin[131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX, enestroburin {Proc.BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX, fluoxastrobin[361377-29-9]+TX, kresoxim-methyl [143390-89-0]+TX, metominostrobin[133408-50-1]+TX, trifloxystrobin [141517-21-7]+TX, orysastrobin[248593-16-0]+TX, picoxystrobin [117428-22-5]+TX, pyraclostrobin[175013-18-0]+TX, ferbam [14484-64-1]+TX, mancozeb [8018-01-7]+TX, maneb[12427-38-2]+TX, metiram [9006-42-2]+TX, propineb [12071-83-9]+TX,thiram [137-26-8]+TX, zineb [12122-67-7]+TX, ziram [137-30-4]+TX,captafol [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid[1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet [133-07-3]+TX,tolylfluanid [731-27-1]+TX, bordeaux mixture [8011-63-0]+TX,copperhydroxid [20427-59-2]+TX, copperoxychlorid [1332-40-7]+TX,coppersulfat [7758-98-7]+TX, copperoxid [1317-39-1]+TX, mancopper[53988-93-5]+TX, oxine-copper [10380-28-6]+TX, dinocap [131-72-6]+TX,nitrothal-isopropyl [10552-74-6]+TX, edifenphos [17109-49-8]+TX,iprobenphos [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen[36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl[57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX, anilazine[101-05-3]+TX, benthiavalicarb [413615-35-7]+TX, blasticidin-S[2079-00-7]+TX, chinomethionat [2439-01-2]+TX, chloroneb [2675-77-6]+TX,chlorothalonil [1897-45-6]+TX, cyflufenamid [180409-60-3]+TX, cymoxanil[57966-95-7]+TX, dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX,diclomezine [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb[87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-L190 (Flumorph)[211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam [162650-77-3]+TX,etridiazole [2593-15-9]+TX, famoxadone [131807-57-3]+TX, fenamidone[161326-34-7]+TX, fenoxanil [115852-48-7]+TX, fentin [668-34-8]+TX,ferimzone [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide[239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid[126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol[10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916 (Cyazofamid)[120116-88-3]+TX, kasugamycin [6980-18-3]+TX, methasulfocarb[66952-49-6]+TX, metrafenone [220899-03-6]+TX, pencycuron[66063-05-6]+TX, phthalide [27355-22-2]+TX, polyoxins [11113-80-7]+TX,probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX, proquinazid[189278-12-4]+TX, pyroquilon [57369-32-1]+TX, quinoxyfen[124495-18-7]+TX, quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX,tiadinil [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tricyclazole[41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin [37248-47-8]+TX,zoxamide (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,isopyrazam [881685-58-1]+TX, sedaxane [874967-67-6]+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide(disclosed in WO 2007/048556)+TX,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO2006/087343)+TX,[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate[915972-17-7]+TX and1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide[926914-55-8]+TX,

or a biologically active compound selected from the group consisting ofN-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide+TX,2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-e]dipyrrole-1,3,5,7(2H,6H)-tetrone+TX,4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine+TX,3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide+TX,CAS 850881-30-0+TX,3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole1,1-dioxide+TX, 2-[2-[(2,5-di methylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide+TX,3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone+TX,2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol+TX,Oxathiapiprolin+TX, tert-butylN-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX,N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide+TX,3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide+TX,2,2,2-trifluoroethylN-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbamate+TX,(2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol+TX,(2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol+TX,2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,N′-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine+TX,[2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate+TX, but-3-ynylN-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX,methylN-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate+TX,3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine+TX,3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine+TX,3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide+TX,1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one+TX,1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one+TX,and

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “development code”is used or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of the compounds of formula I selectedfrom A1 to A1 8 (above) with active ingredients described abovecomprises a compound selected from A1 to A18 (above) and an activeingredient as described above preferably in a mixing ratio of from 100:1to 1:6000, especially from 50:1 to 1:50, more especially in a ratio offrom 20:1 to 1:20, even more especially from 10:1 to 1:10, veryespecially from 5:1 and 1:5, special preference being given to a ratioof from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewisepreferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4,or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5,or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75,or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750,or 2:750, or 4:750. Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of formula I selected from A1 to A1 8(above) and one or more active ingredients as described above can beapplied, for example, in a single “ready-mix” form, in a combined spraymixture composed from separate formulations of the single activeingredient components, such as a “tank-mix”, and in a combined use ofthe single active ingredients when applied in a sequential manner, i.e.one after the other with a reasonably short period, such as a few hoursor days. The order of applying the compounds of formula I selected fromA1 to A1 8 (above) and the active ingredients as described above is notessential for working the present invention.

The compositions according to the invention can also comprise furthersolid or liquid auxiliaries, such as stabilizers, for exampleunepoxidized or epoxidized vegetable oils (for example epoxidizedcoconut oil, rapeseed oil or soya oil), antifoams, for example siliconeoil, preservatives, viscosity regulators, binders and/or tackifiers,fertilizers or other active ingredients for achieving specific effects,for example bactericides, fungicides, nematocides, plant activators,molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds I for the preparation of these compositions are also asubject of the invention.

Another aspect of invention is related to the use of a compound offormula I or of a preferred individual compound as above-defined, of acomposition comprising at least one compound of formula I or at leastone preferred individual compound as above-defined, or of a fungicidalor insecticidal mixture comprising at least one compound of formula I orat least one preferred individual compound as above-defined, inadmixture with other fungicides or insecticides as described above, forcontrolling or preventing infestation of plants, e.g. useful plants suchas crop plants, propagation material thereof, e.g. seeds, harvestedcrops, e.g. harvested food crops, or non-living materials by insects orby phytopathogenic microorganisms, preferably fungal organisms.

A further aspect of invention is related to a method of controlling orpreventing an infestation of plants, e.g. useful plants such as cropplants, propagation material thereof, e.g. seeds, harvested crops, e.g.harvested food crops, or of non-living materials by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, which comprises theapplication of a compound of formula I or of a preferred individualcompound as above-defined as active ingredient to the plants, to partsof the plants or to the locus thereof, to the propagation materialthereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, to such a level that animprovement is demonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,or insects which comprises the application of a compound of formula I,or an agrochemical composition which contains at least one of saidcompounds, is foliar application. The frequency of application and therate of application will depend on the risk of infestation by thecorresponding pathogen or insect. However, the compounds of formula Ican also penetrate the plant through the roots via the soil (systemicaction) by drenching the locus of the plant with a liquid formulation,or by applying the compounds in solid form to the soil, e.g. in granularform (soil application). In crops of water rice such granulates can beapplied to the flooded rice field. The compounds of formula I may alsobe applied to seeds (coating) by impregnating the seeds or tubers eitherwith a liquid formulation of the fungicide or coating them with a solidformulation.

A formulation, e.g. a composition containing the compound of formula I,and, if desired, a solid or liquid adjuvant or monomers forencapsulating the compound of formula I, may be prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally, surfaceactive compounds (surfactants).

The application methods for the compositions, that is the methods ofcontrolling pests of the abovementioned type, such as spraying,atomizing, dusting, brushing on, dressing, scattering or pouring—whichare to be selected to suit the intended aims of the prevailingcircumstances—and the use of the compositions for controlling pests ofthe abovementioned type are other subjects of the invention. Typicalrates of concentration are between 0.1 and 1000 ppm, preferably between0.1 and 500 ppm, of active ingredient. The rate of application perhectare is preferably 1 g to 2000 g of active ingredient per hectare,more preferably 10 to 1000 g/ha, most preferably 10 to 600 g/ha. Whenused as seed drenching agent, convenient dosages are from 10 mg to 1 gof active substance per kg of seeds.

When the combinations of the present invention are used for treatingseed, rates of 0.001 to 50 g of a compound of formula I per kg of seed,preferably from 0.01 to 10 g per kg of seed are generally sufficient.

Suitably, a composition comprising a compound of formula (I) accordingto the present invention is applied either preventative, meaning priorto disease development or curative, meaning after disease development.

The compositions of the invention may be employed in any conventionalform, for example in the form of a twin pack, a powder for dry seedtreatment (DS), an emulsion for seed treatment (ES), a flowableconcentrate for seed treatment (FS), a solution for seed treatment (LS),a water dispersible powder for seed treatment (WS), a capsule suspensionfor seed treatment (CF), a gel for seed treatment (GF), an emulsionconcentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE),a capsule suspension (CS), a water dispersible granule (WG), anemulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion,oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oilmiscible flowable (OF), an oil miscible liquid (OL), a solubleconcentrate (SL), an ultra-low volume suspension (SU), an ultra-lowvolume liquid (UL), a technical concentrate (TK), a dispersibleconcentrate (DC), a wettable powder (WP) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g. by mixingthe active ingredients with appropriate formulation inerts (diluents,solvents, fillers and optionally other formulating ingredients such assurfactants, biocides, anti-freeze, stickers, thickeners and compoundsthat provide adjuvancy effects). Also conventional slow releaseformulations may be employed where long lasting efficacy is intended.Particularly formulations to be applied in spraying forms, such as waterdispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like),wettable powders and granules, may contain surfactants such as wettingand dispersing agents and other compounds that provide adjuvancyeffects, e.g. the condensation product of formaldehyde with naphthalenesulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkylsulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to theseeds employing the combination of the invention and a diluent insuitable seed dressing formulation form, e.g. as an aqueous suspensionor in a dry powder form having good adherence to the seeds. Such seeddressing formulations are known in the art. Seed dressing formulationsmay contain the single active ingredients or the combination of activeingredients in encapsulated form, e.g. as slow release capsules ormicrocapsules.

In general, the formulations include from 0.01 to 90% by weight ofactive agent, from 0 to 20% agriculturally acceptable surfactant and 10to 99.99% solid or liquid formulation inerts and adjuvant(s), the activeagent consisting of at least the compound of formula I together withcomponent (B) and (C), and optionally other active agents, particularlymicrobiocides or conservatives or the like. Concentrated forms ofcompositions generally contain in between about 2 and 80%, preferablybetween about 5 and 70% by weight of active agent. Application forms offormulation may for example contain from 0.01 to 20% by weight,preferably from 0.01 to 5% by weight of active agent. Whereas commercialproducts will preferably be formulated as concentrates, the end userwill normally employ diluted formulations.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

EXAMPLES

The Examples which follow serve to illustrate the invention. Certaincompounds of the invention can be distinguished from known compounds byvirtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppmor 0.2 ppm.

Throughout this description, temperatures are given in degrees Celsiusand “m.p.” means melting point. LC/MS means Liquid Chromatography MassSpectroscopy and the description of the apparatus and the methods are:

Method G:

Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters(SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with anelectrospray source (Polarity: positive or negative ions, Capillary:3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature:150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr,Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and anAcquity UPLC from Waters: Binary pump, heated column compartment anddiode-array detector. Solvent degasser, binary pump, heated columncompartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8μm, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500,Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05%HCOOH, gradient: 10-100% B in 1.2 min; Flow (ml/min) 0.85

Method H:

Spectra were recorded on a Mass Spectrometer (ACQUITY UPLC) from Waters(SQD, SQDII or ZQ Single quadrupole mass spectrometer) equipped with anelectrospray source (Polarity: positive or negative ions, Capillary:3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature:150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 0 L/Hr,Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and anAcquity UPLC from Waters: Binary pump, heated column compartment anddiode-array detector. Solvent degasser, binary pump, heated columncompartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8μm, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500,Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05%HCOOH, gradient: 10-100% B in 2.7 min; Flow (ml/min) 0.85

Formulation Examples

Wettable powders a) b) c) active ingredient [compound of formula (I)]25% 50% 75% sodium lignosulfonate 5% 5% — sodium lauryl sulfate 3% —  5%sodium diisobutylnaphthalenesulfonate — 6% 10% phenol polyethyleneglycol ether — 2% — (7-8 mol of ethylene oxide) highly dispersed silicicacid 5% 10% 10% Kaolin 62% 27% —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders that can be diluted with water to give suspensions of thedesired concentration.

Powders for dry seed treatment a) b) c) active ingredient [compound offormula (I)] 25% 50% 75% light mineral oil 5% 5%  5% highly dispersedsilicic acid 5% 5% — Kaolin 65% 40% — Talcum — 20

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording powders thatcan be used directly for seed treatment.

Emulsifiable concentrate active ingredient [compound of formula (I)] 10%octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide)calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (35 molof ethylene oxide) 4% Cyclohexanone 30% xylene mixture 50%

Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts a) b) c) Active ingredient [compound of formula (I)]  5%  6%  4%talcum 95% — — Kaolin — 94% — mineral filler — — 96%

Ready-for-use dusts are obtained by mixing the active ingredient withthe carrier and grinding the mixture in a suitable mill. Such powderscan also be used for dry dressings for seed.

Extruder granules Active ingredient [compound of formula (I)] 15% sodiumlignosulfonate 2% carboxymethylcellulose 1% Kaolin 82%

The active ingredient is mixed and ground with the adjuvants, and themixture is moistened with water. The mixture is extruded and then driedin a stream of air.

Coated granules Active ingredient [compound of formula (I)] 8%polyethylene glycol (mol. wt. 200) 3% Kaolin 89%

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

Suspension concentrate active ingredient [compound of formula (I)] 40%propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol ofethylene oxide) 6% Sodium lignosulfonate 10% carboxymethylcellulose 1%silicone oil (in the form of a 75% emulsion in water) 1% Water 32%

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Flowable concentrate for seed treatment active ingredient [compound offormula (I)] 40%  propylene glycol 5% copolymer butanol PO/EO 2%tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (inthe form of a 20% solution 0.5%   in water) monoazo-pigment calcium salt5% Silicone oil (in the form of a 75% emulsion in water) 0.2%   Water45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Slow Release Capsule Suspension

28 parts of a combination of the compound of formula I are mixed with 2parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of athickener and 3 parts of a dispersing agent. The capsule suspensionformulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspensionin an apparatus suitable for that purpose.

PREPARATION EXAMPLES Example 1: this Example Illustrates the Preparationof5-fluoro-3,3,4,4-tetramethyl-1-(4-methylbenzimidazol-1-yl)isoquinolineStep 1: Preparation of ethyl-2-(2-fluorophenyl)-2-methyl-propanoate

To a suspension of sodium hydride (0.69 mol, 27.4 g) in tetrahydrofuran(220 mL) at room temperature was added dropwise a solution ofethyl-2-(2-fluorophenyl)acetate (0.27 mol, 50.0 g) and iodomethane (0.82mmol, 117.9 g) in tetrahydrofuran (60 mL, conc. Total 1 M) and themixture was stirred at room temperature overnight. The reaction wasquenched by the slow addition of a saturated aqueous solution ammoniumchloride and then poured into 300 mL of ice-water mixture. The aqueousphase was extracted with ethyl acetate, and the combined organicextracts were dried over sodium sulfate, filtered and concentrated underreduced pressure. The residue was purified by flash chromatography(heptane/ethyl acetate=19:1) to giveethyl-2-(2-fluorophenyl)-2-methyl-propanoate as a pale yellow oil: LC-MS(Method H) UV Detection: 220 nm, Rt=1.60; MS: (M+1)=211.2; ¹H NMR (400MHz, CHLOROFORM-d) δ ppm 1.16-1.23 (m, 3H) 1.57 (s, 6H) 4.17 (d, J=6.97Hz, 2H) 6.99-7.05 (m, 1H) 7.11-7.17 (m, 1H) 7.22-7.28 (m, 1H) 7.33 (td,J=7.89, 1.83 Hz, 1H); ¹⁹F NMR (377 MHz, CHLOROFORM-d) δ ppm −113.26 (s,1F).

Step 2: Preparation of 3-(2-fluorophenyl)-2,3-dimethyl-butan-2-ol

A solution of ethyl-2-(2-fluorophenyl)-2-methyl-propanoate (0.25 mol,52.1 g) and lanthanum(III) chloride bis(lithium chloride) complex (0.6 Min THF, 0.50 equiv., 0.12 mol, 207 mL) in tetrahydrofuran (1.2 M) wasstirred at room temperature for 1.5 h. The reaction was then cooled to0° C. and a solution of methyl magnesium bromide (3.0 M in diethylether, 3.0 equiv, 0.74 mol, 248 mL) was subsequently added dropwise. Thereaction mixture was stirred at room temperature overnight, cooled to 0°C. and then quenched by the dropwise addition of a saturated aqueoussolution of ammonium chloride solution. Water was added and the reactionmixture was stirred for an additional 30 min. The reaction mixture wasfiltered over Celite and the two phases were separated. The aqueousphase was extracted with tert-butyl methyl ether, and the combinedorganic phases were washed with brine, dried over sodium sulfate,filtered and concentrated under reduced pressure to give3-(2-fluorophenyl)-2,3-dimethyl-butan-2-ol as a yellowish solid: LC-MS(Method H) UV Detection: 220 nm, Rt=1.46; MS: (M-OH)=179.3; m.p. 42-43°C.; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.19 (d, J=1.10 Hz, 6H) 1.50(d, J=2.93 Hz, 6H) 6.97-7.04 (m, 1H) 7.07-7.12 (m, 1H) 7.18-7.24 (m, 1H)7.40 (td, J=8.25, 1.83 Hz, 1H); ¹⁹F NMR (377 MHz, CHLOROFORM-d) δ ppm−104.04 (s, 1F).

Step 3: Preparation of5-fluoro-3,3,4,4-tetramethyl-1-methylsulfanyl-isoquinoline

To cooled (0° C.) sulfuric acid (98% w/w, 133 mL, 1 M) was added amixture of methyl thiocyanate (133 mmol, 9.73 g) and3-(2-fluorophenyl)-2,3-dimethyl-butan-2-ol (1.00 equiv., 133 mmol, 26.1g) portion-wise over 15 min, and the mixture was stirred at roomtemperature for additional 20 min. The reaction mixture was carefullypoured into 600 ml ice water and the pH of the water layer was adjustedto ˜8 using an aqueous solution of NaOH (30% w/w). The aqueous phase wasextracted with ethyl acetate and the combined organic phases were driedwith Na₂SO₄, filtered and concentrated in vacuo to afford (25.1 g, 75%)of 5-fluoro-3,3,4,4-tetramethyl-1-methylsulfanyl-isoquinoline as a paleyellow oil: LC-MS (Method G) UV Detection: 220 nm, Rt=; MS: (M+1)=; ¹HNMR (400 MHz, CHLOROFORM-d) δ ppm 1.10 (s, 6H) 1.24 (d, J=2.93 Hz, 6H)2.34 (s, 3H) 7.00 (ddd, J=12.20, 8.34, 1.10 Hz, 1H) 7.07-7.21 (m, 1H)7.32-7.42 (m, 1H); ¹⁹F NMR (377 MHz, CHLOROFORM-d) δ ppm −111.06 (s,1F).

Step 4: Preparation of 5-fluoro-3,3,4,4-tetramethyl-2H-isoquinolin-1-one

To a solution of5-fluoro-3,3,4,4-tetramethyl-1-methylsulfanyl-isoquinoline (99.8 mmol,25.1 g) in a mixture of acetic acid (160 mL, 0.25 M) and water (40 mL)was added sodium acetate (0.10 equiv., 9.98 mmol, 0.818 g) and themixture was heated at reflux for 2 h. The reaction mixture was thencooled down to room temperature and most of the acetic acid solution wasremoved under vacuo. The residue was then carefully added to a mixtureof saturated aqueous NaHCO₃ and ethyl acetate. The two layers wereseparated and the aqueous layer was extracted with ethyl acetate. Thecombined organic phases were washed with saturated aqueous NaHCO₃, waterand brine, dried with Na₂SO₄, filtered and concentrated in vacuo toafford 5-fluoro-3,3,4,4-tetramethyl-2H-isoquinolin-1-one (21.4 g, 97%)as a pale yellow oil: LC-MS (Method G) UV Detection: 220 nm, Rt=1.28;MS: (M+1)=222.2; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.21 (s, 6H) 1.36(d, J=1.00 Hz, 6H) 6.19 (br. s, 1H) 7.12 (ddd, J=12.38, 8.34, 1.28 Hz,1H) 7.20-7.26 (m, 1H) 7.85 (dd, J=7.52, 1.28 Hz, 1H); ¹⁹F NMR (377 MHz,CHLOROFORM-d) δ ppm −111.05 (s, 1F).

Step 5: Preparation of1-chloro-5-fluoro-3,3,4,4-tetramethyl-isoquinoline

To a solution of N,N-dimethylformamide (6.3 mmol, 0.49 mL) indichloromethane (8 mL, 0.8 M) at room temperature was added oxalylchloride (1.3 equiv., 6.01 mmol, 0.53 mL) dropwise and the whitesuspension was vigorously stirred for 30 min. A solution of5-fluoro-3,3,4,4-tetramethyl-2H-isoquinolin-1-one (4.52 mmol, 1.00 g) indichloromethane (9 mL, 0.5 M) was then added dropwise and the mixturewas stirred at room temperature for 2h. The reaction mixture was pouredinto an ice-cooled mixture of saturated aqueous NaHCO₃ solution andpentane, and the organic phase was separated. The aqueous phase was thenextracted with pentane, and the combined organic phases were washed withbrine, dried over Na₂SO₄, filtered and concentrated to give1-chloro-5-fluoro-3,3,4,4-tetramethyl-isoquinoline (1.02 g, 94% yield)as a colourless oil: LC-MS (Method G) UV Detection: 220 nm, Rt=1.16; MS:(M+1)=240-242; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.27 (s, 6H) 1.38(s, 6H) 7.15-7.20 (m, 1H) 7.26-7.36 (m, 1H) 7.62 (d, 1H).

Step 6: Preparation of5-fluoro-3,3,4,4-tetramethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline

To a solution of 1-chloro-5-fluoro-3,3,4,4-tetramethyl-isoquinoline(1.67 mmol, 0.430 g) in pyridine (0.20 M, 9.0 mL) at room temperaturewas added 4-methyl-1H-benzimidazole (1.5 equiv., 2.69 mmol, 0.356 g) andthe mixture was stirred at 90° C. for 15 hours. The reaction mixture wasallowed to cool down to room temperature and then concentrated undervacuo. The residue obtained was purified by flash chromatography to give5-fluoro-3,3,4,4-tetramethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline(0.525 g, 87% yield) as a beige solid: mp=118-120° C., LC-MS (Method G)UV Detection: 220 nm, Rt=1.19, MS: (M+1)=336; ¹H NMR (400 MHz,CHLOROFORM-d) δ ppm 1.32 (s, 6H) 1.47 (s, 6H) 2.71 (s, 3H) 6.91-6.95 (m,1H) 7.10-7.25 (m, 5H) 8.18 (s, 1H).

Example 2: This Example Illustrates the Preparation of4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline Step1: Preparation of 3,3-dimethyl-2H-isoquinoline-1,4-dione

To a solution of 3,3-dimethyl-2,4-dihydroisoquinolin-1-one (57.1 mmol,10.0 g) in CCl₄ (0.20 M, 285 mL) at room temperature was addedN-bromosuccinimide (3.0 equiv., 171 mmol, 30.5 g) and AIBN (0.15 equiv.,8.5 mmol, 1.43 g) and the reaction mixture was stirred at 70° C. for 3hours. The reaction mixture was allowed to cool down to roomtemperature, concentrated under vacuo and diluted with EtOAc, washedwith water and brine, dried over Na₂SO₄, filtered and concentrated togive 4,4-dibromo-3,3-dimethyl-2H-isoquinolin-1-one (25.2 g) as a lightyellow solid which was used directly in the next step without furtherpurification: LC-MS (Method H) UV Detection: 220 nm, Rt=1.34; MS:(M+1)=332-334-336; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.57 (s, 6H)7.21 (br. s, 1H) 7.70-7.77 (m, 1H) 7.78-7.85 (m, 1H) 8.06-8.14 (m, 1H)8.23-8.30 (m, 1H).

To a solution of 4,4-dibromo-3,3-dimethyl-2H-isoquinolin-1-one (20.0 g)in a mixture of water (450 mL) and tetrahydrofuran (225 mL) was addedsodium carbonate (3.0 equiv., 135 mmol, 14.3 g) and the mixture wasstirred at room temperature for 12 h and at 70° C. for 4 h 30 min. Thereaction mixture was allowed to cool down to room temperature, dilutedwith water, acidified to PH 3-4 with 90 mL of a 2 M solution ofhydrochloric acid and extracted with dichloromethane. The combinedorganic extracts were dried over Na₂SO₄, filtered and concentrated togive 3,3-dimethyl-2H-isoquinoline-1,4-dione (9.95 g) as a yellow solid:LC-MS (Method H) UV Detection: 220 nm, Rt=0.81; MS: (M+1)=190; ¹H NMR(400 MHz, CHLOROFORM-d) δ ppm 1.77 (s, 3H) 1.97 (s, 3H) 7.39 (s, 1H)7.46-7.58 (m, 1H) 7.60-7.71 (m, 1H) 7.98-8.22 (m, 2H).

Step 2: Preparation of 1-chloro-3,3-dimethyl-isoquinolin-4-one

To a solution of N,N-dimethylformamide (2.3 mL, 30 mmol) indichloromethane (52 mL, 0.6 M) at room temperature was added oxalylchloride (0.67 equiv., 20 mmol, 1.8 mL) dropwise over a period of 35 minand the white suspension was vigorously stirred for 15 min until the gasevolution stopped. A solution of 3,3-dimethyl-2H-isoquinoline-1,4-dione(2.5 g, 13 mmol) in dichloromethane (25 mL) was then added dropwise andthe mixture was stirred at room temperature for 1 h. The reactionmixture was poured into an ice-cooled mixture of saturated aqueousNaHCO₃ solution and pentane, and the organic phase was separated. Theaqueous phase was then extracted with pentane, and the combined organicphases were washed with brine, dried over Na₂SO₄, filtered andconcentrated to give 1-chloro-3,3-dimethyl-isoquinolin-4-one (2.5 g, 91%yield) as a yellow solid: LC-MS (Method H) UV Detection: 220 nm,Rt=1.34; MS: (M+1)=208-210; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47(s, 6H) 7.62-7.69 (m, 1H) 7.73-7.81 (m, 1H) 7.90 (dd, J=8.07, 0.73 Hz,1H) 8.04 (dd, J=7.50, 0.90 Hz, 1H).

Step 3: Preparation of3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinolin-4-one

To a solution of 1-chloro-3,3-dimethyl-isoquinolin-4-one (3.61 mmol,0.750 g) in pyridine (0.07 M, 50 mL) at room temperature was added4-methyl-1H-benzimidazole (1.5 equiv., 0.716 g, 5.42 mmol) and themixture was stirred at 100° C. for 15 hours. The reaction mixture wasallowed to cool down to room temperature and then concentrated undervacuo. The residue obtained was purified by flash chromatography to give3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinolin-4-one (0.569 g,52% yield) as a brown oil: LC-MS (Method G) UV Detection: 220 nm,Rt=0.98, MS: (M+1)=305; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.63 (s,6H) 2.75 (s, 3H) 7.15-7.27 (m, 3H) 7.36-7.42 (m, 1H) 7.70-7.82 (m, 2H)8.18-8.25 (m, 1H) 8.28 (s, 1H).

Step 4: Preparation of4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline

A solution of3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinolin-4-one (1.85 mmol,560 mg) in 2,2-difluoro-1,3-dimethyl-imidazolidine (10.0 equiv., 18.5mmol, 2.4 mL) was stirred at 105° C. overnight. The reaction mixture wasallowed to cool down to room temperature, diluted with DCM then quenchedby slow addition to a saturated aqueous NaHCO₃ solution. The 2 phaseswere separated, and the aqueous phase was extracted with DCM. Thecombined organic phases were washed with brine, dried over Na₂SO₄,filtered and concentrated. The residue was purified by flashchromatography to give4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline (36mg, 60% yield) as a white solid: LC-MS (Method G) UV Detection: 220 nm,Rt=1.12; MS: (M+1)=326; mp 142-149° C.; ¹H NMR (400 MHz, CHLOROFORM-d) δppm 1.49 (s, 6H) 2.76 (s, 3H) 7.15-7.27 (m, 2H) 7.34-7.42 (m, 2H)7.57-7.64 (m, 1H) 7.71-7.79 (m, 1H) 7.90-7.97 (m, 1H) 8.31 (s, 1H); ¹⁹FNMR (377 MHz, CHLOROFORM-d) δ ppm-112.38 (br. s., 1F).

Example 3: This Example Illustrates the Preparation of1′-(benzimidazol-1-yl)-3′,3′-dimethyl-spiro(cyclopropane-1,4′-isoquinoline)Step 1: Preparation of3,3-dimethylspiro(2H-isoquinoline-4,1′-cyclopropane)-1-one

In an autoclave was added a solution of2-(1-phenylcyclopropyl)propan-2-amine (120 mg, 0.685 mmol), benzoquinone(2.0 equiv., 1.37 mmol, 153 mg) and palladium (II) acetate (0.05 equiv.,0.034 mmol, 7.6 mg) in acetic acid (4.6 mL, 0.15 M) and the highpressure reactor was pressurized with carbon monoxide (3 bars) andheated at 110° C. overnight. The reaction vessel was allowed to cooldown to room temperature, depressurized and the reaction mixture wasdiluted with dichloromethane and quenched by the addition of an aqueousNaOH solution (2.0 M) to reach pH>9. The two phases were separated andthe aqueous phase was extracted with dichloromethane twice. The combinedorganic phases were washed with brine, dried over Na₂SO₄, filtered,concentrated and purified by flash chromatography to give3,3-dimethylspiro(2H-isoquinoline-4,1′-cyclopropane)-1-one (27 mg, 20%yield) as a yellowish gum: LC-MS (Method G), Rt=0.80; MS: (M+1)=202; ¹HNMR (400 MHz, CHLOROFORM-d) δ ppm 0.96 (t, 2H) 1.10 (t, 2H) 1.18 (s, 6H)6.21 (NH, 1H) 6.91 (d, 1H) 7.20 (t, 1H) 7.45 (t, 1H) 8.09 (d, 1H).

Step 2: Preparation of1′-chloro-3′,3′-dimethyl-spiro(cyclopropane-1,4′-isoquinoline)

To a solution of N,N-dimethylformamide (0.63 mmol, 0.049 mL) indichloromethane (1 mL, 0.5 M) at room temperature was added oxalylchloride (1.3 equiv., 0.63 mmol, 0.056 mL) dropwise and the whitesuspension was vigorously stirred for 30 min. A solution of3,3-dimethylspiro(2H-isoquinoline-4,1′-cyclopropane)-1-one (0.423 mmol,85 mg) in dichloromethane (0.8 mL, conc. total 0.25 M) was then addeddropwise and the mixture was stirred at room temperature for 1 h. Thereaction mixture was poured into an ice-cooled mixture of saturatedaqueous NaHCO₃ solution and pentane, and the organic phase wasseparated. The aqueous phase was then extracted with pentane, and thecombined organic phases were washed with brine, dried over Na₂SO₄,filtered and concentrated to give1′-chloro-3′,3′-dimethyl-spiro(cyclopropane-1,4′-isoquinoline) (101 mg,98% yield) as a beige liquid: LC-MS (Method G), Rt=1.06; MS:(M+1)=220-222.

Step 3: Preparation of1′-(benzimidazol-1-yl)-3′,3′-dimethyl-spiro(cyclopropane-1,4′-isoquinoline)

To a solution of1′-chloro-3′,3′-dimethyl-spiro(cyclopropane-1,4′-isoquinoline) (0.064mmol, 14 mg) in pyridine (1.3 mL, 0.05M) was added benzimidazole (5equiv., 0.32 mmol, 38 mg) and the mixture was stirred at 90° C. for 1 h.The reaction mixture was allowed to cool down to room temperature andthen concentrated under vacuo. The residue obtained was purified byflash chromatography to give1′-(benzimidazol-1-yl)-3′,3′-dimethyl-spiro(cyclopropane-1,4′-isoquinoline)(9 mg, 50% yield) as a yellow gum: LC-MS (Method G), Rt=1.04; MS:(M+1)=302; ¹H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.01 (t, 2H) 1.17 (t,2H) 1.23 (s, 6H) 7.08 (d, 1H) 7.15-7.24 (m, 2H) 7.27-7.35 (m, 2H) 7.48(t, 1H) 7.52 (d, 1H) 7.84 (d, 1H) 8.30 (s, 1H).

TABLE E Physical data of compounds of formula I [M + H] Entry STRUCTURERT (min) (measured) Method MP ° C. E-1

1.15 336.4 G 45-46 E-2

1.13 322.5 G E-3

1.04 302 G E-4

1.22 401.3 G 48-49 E-5

1.25 390.5 G E-6

1.13 352.5 G E-7

1.17 340.4 G E-8

1.26 362.5 G E-9

1.10 316 G E-10

0.96 304 G 123-125 E-11

1.30 362.5 G E-12

1.31 364.5 G 113-114 E-13

1.25 348.4 G 70-71 E-14

1.25 350.5 G 87-88 E-15

1.10 326 G E-16

1.14 318 G E-17

1.21 356.4 G 50-51 E-18

1.19 350.6 G E-19

1.13 358 G 157-159 E-20

1.08 344 G E-21

1.14 340.5 G E-22

1.18 354.5 G E-23

1.13 340.5 G 132-133 E-24

1.10 380.4 G 178-179 E-25

0.99 318.4 G 159-161 E-26

1.03 318.5 G  96-101 E-27

1.07 332.5 G 145-149 E-28

1.81 347 H 199-202 E-29

1.51 325 H E-30

1.21 351 G E-31

1.92 362 H E-32

1.16 344 G 118-121 E-33

1.23 361 G E-34

1.71 339 H 129-133 E-35

1.80 357 H 133-136 E-36

1.83 353 H 196-199 E-37

2.00 381 H 197-200 E-38

1.19 369 G 52-54 E-39

1.32 391 G 126-127 E-40

1.17 324 G E-41

1.33 415 G 122-124 E-42

1.31 370 G 102-103 E-43

1.12 302 G 132-133 E-44

1.07 290 G E-45

1.27 370 G 147-151 E-46

1.21 354 G 122-125 E-47

1.99 361 H E-48

2.06 379 H E-49

2.10 375 H E-50

1.23 358 G 112-114 E-51

1.27 362 G 177-178 E-52

1.27 330 G E-53

1.20 316 G E-54

0.81 302 G E-55

1.88 352 H E-56

1.92 358 H E-57

1.75 322 H 143-145 E-58

1.14 328 G 141-143 E-59

1.06 288 G E-60

1.24 354 G E-61

1.11 314 G

Biological Examples

Botryotinia Fuckeliana (Botrytis cinerea)/Liquid Culture (Gray Mould)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (Vogels broth). After placing a (DMSO) solution of testcompound into a microtiter plate (96-well format), the nutrient brothcontaining the fungal spores is added. The test plates are incubated at24° C. and the inhibition of growth is determined photometrically 3-4days after application.

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-1, E-2, E-3,E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-14, E-15, E-16,E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-25, E-26, E-27, E-29, E-30,E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42,E-43, E-44, E-45, E-46, E-47, E-48, E-49, E-50, E-51, E-52, E-53, E-54,E-55, E-56, E-57, E-58, E-59, E-60, E-61

Fusarium culmorum/Liquid Culture (Head Blight)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 3-4 days after application.

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-1, E-2, E-4,E-7, E-9, E-14, E-15, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23,E-25, E-26, E-27, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-41, E-42,E-45, E-46, E-47, E-48, E-49, E-50, E-51, E-55, E-56, E-57, E-58, E-59,E-60, E-61

Gaeumannomyces graminis/Liquid Culture (Take-all of Cereals)

Mycelial fragments of the fungus from cryogenic storage were directlymixed into nutrient broth (PDB potato dextrose broth). After placing a(DMSO) solution of test compound into a microtiter plate (96-wellformat), the nutrient broth containing the fungal spores is added. Thetest plates are incubated at 24° C. and the inhibition of growth isdetermined photometrically 4-5 days after application.

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-1, E-3, E-4,E-7, E-8, E-9, E-14, E-15, E-16, E-17, E-18, E-19, E-21, E-23, E-30,E-31, E-32, E-33, E-37, E-41, E-47, E-48, E-49, E-51, E-58, E-59, E-60,E-61

Glomerella Lagenarium (Colletotrichum lagenarium)/Liquid Culture(Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is measuredphotometrically 3-4 days after application.

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-1, E-2, E-3,E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-14, E-15, E-16,E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-25, E-26, E-27, E-30, E-31,E-32, E-33, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, E-46, E-49,E-50, E-54, E-55, E-56, E-57, E-58, E-59, E-60, E-61

Monographella nivalis (Microdochium nivale)/Liquid Culture (Foot RotCereals)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 4-5 days after application.

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-1, E-2, E-4,E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17,E-18, E-19, E-20, E-21, E-22, E-23, E-25, E-26, E-27, E-30, E-31, E-32,E-33, E-34, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, E-46,E-47, E-48, E-49, E-50, E-51, E-53, E-54, E-55, E-56, E-57, E-58, E-59,E-60, E-61

Mycosphaerella graminicola (Septoria tritici)/Liquid Culture (SeptoriaBlotch)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 4-5 days after application.

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-1, E-18, E-21,E-22, E-30, E-32, E-33, E-34, E-35, E-36, E-50, E-53, E-54, E-55, E-56,E-57, E-60

Magnaporthe grisea (Pyricularia oryzae)/Rice/Leaf Disc Preventative(Rice Blast)

Rice leaf segments cv. Ballila are placed on agar in a multiwell plate(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf segments are inoculated with a spore suspension ofthe fungus 2 days after application. The inoculated leaf segments areincubated at 22° C. and 80% r.h. under a light regime of 24 h darknessfollowed by 12 h light/12 h darkness in a climate cabinet and theactivity of a compound is assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf segments (5-7 days after application).

The following compounds of Table E gave at least 80% disease control at200 ppm when compared to untreated control leaf disks under the sameconditions, which show extensive disease development: E-21, E-42, E-49,E-50

Magnaporthe grisea (Pyricularia oryzae)/Liquid Culture (Rice Blast)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 3-4 days after application.

The following compounds gave at least 80% control of Magnaporthe griseaat 20 ppm when compared to untreated control under the same conditions,which showed extensive disease development: E-1, E-4, E-5, E-6, E-7,E-8, E-9, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17, E-18, E-19,E-20, E-21, E-22, E-23, E-24, E-25, E-26, E-27, E-30, E-31, E-32, E-33,E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45,E-46, E-47, E-48, E-49, E-50, E-51, E-52, E-53, E-54, E-55, E-56, E-57,E-58, E-59, E-60, E-61

Fusarium culmorum/Wheat/Spikelet Preventative (Head Blight)

Wheat spikelets cv. Monsun are placed on agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The spikelets are inoculated with a spore suspension of thefungus 1 day after application. The inoculated spikelets are incubatedat 20° C. and 60% rh under a light regime of 72 h semi darkness followedby 12 h light/12 h darkness in a climate chamber and the activity of acompound is assessed as percent disease control compared to untreatedwhen an appropriate level of disease damage appears on untreated checkspikelets (6-8 days after application).

The following compounds gave at least 80% control of Fusarium culmorumat 200 ppm when compared to untreated control under the same conditions,which showed extensive disease development: E-20, E-46, E-49, E-56, E-58

Pyrenophora teres/Barley/Leaf Disc Preventative (Net Blotch)

Barley leaf segments cv. Hasso are placed on agar in a multiwell plate(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf segmens are inoculated with a spore suspension of thefungus 2 days after application. The inoculated leaf segments areincubated at 20° C. and 65% rh under a light regime of 12 h light/12 hdarkness in a climate cabinet and the activity of a compound is assessedas disease control compared to untreated when an appropriate level ofdisease damage appears in untreated check leaf segments (5-7 days afterapplication).

The following compounds gave at least 80% control of Pyrenophora teresat 200 ppm when compared to untreated control under the same conditions,which showed extensive disease development: E-16

Pyrenophora teres/Liquid Culture (Net Blotch)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (Vogels broth). After placing a (DMSO) solution of testcompound into a microtiter plate (96-well format), the nutrient brothcontaining the fungal spores is added. The test plates are incubated at24° C. and the inhibition of growth is determined photometrically 3-4days after application.

The following compounds gave at least 80% control of Pyrenophora teresat 20 ppm when compared to untreated control under the same conditions,which showed extensive disease development: E-1, E-4, E-5, E-6, E-7,E-9, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17, E-18, E-19, E-20,E-21, E-22, E-23, E-25, E-26, E-27

Sclerotinia sclerotiorum/Liquid Culture (Cottony Rot)

Mycelia fragments of a newly grown liquid culture of the fungus aredirectly mixed into nutrient broth (Vogels broth). After placing a(DMSO) solution of test compound into a microtiter plate (96-wellformat) the nutrient broth containing the fungal material is added. Thetest plates are incubated at 24° C. and the inhibition of growth isdetermined photometrically 3-4 days after application.

The following compounds gave at least 80% control of Sclerotiniasclerotiorum at 20 ppm when compared to untreated control under the sameconditions, which showed extensive disease development: E-1, E-15, E-16,E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-25, E-26, E-27, E-30, E-31,E-32, E-33, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, E-46,E-55, E-56, E-57, E-58, E-61

The invention claimed is:
 1. A compound of formula I:

wherein R₁ and R₂ are each independently selected from hydrogen, cyano,C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl and C₂-C₆ alkynyl, in whichthe alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio; or R₁ and R₂ together withthe carbon atom to which they are attached represent a C₃-C₁₀ cycloalkylgroup (which may be optionally substituted with 1 to 3 substituentsindependently selected from the group consisting of halogen, C₁-C₆alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio); R₃ and R₄ are eachindependently selected from hydrogen, halogen, hydroxyl, C₁-C₆ alkyl,C₁-C₆ alkoxy, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl and C₂-C₆ alkynyl, inwhich the alkyl, alkoxy, cycloalkyl, alkenyl and alkynyl groups may beoptionally substituted with 1 to 3 substituents independently selectedfrom halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio; or R₃ and R₄ togetherwith the carbon atom to which they are attached represent C═O,C═NOR_(a), C═C(R_(b))(R_(c)) or C₃-C₁₀ cycloalkyl (which may beoptionally substituted with 1 to 3 substituents independently selectedfrom the group consisting of a halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy andC₁-C₆ alkylthio); or R₂ and R₃ together with the carbon atoms to whichthey are attached represent a C₅-C₁₀cycloalkyl (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆alkylthio, and, additionally, a ring carbon unit may be replaced by anoxygen or sulphur atom); each R₅ independently represents halogen,hydroxyl, mercapto, nitro, cyano, formyl, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆ alkenyloxy, C₃-C₆alkynyloxy, C₁-C₆ alkylthio, —C(═NOR_(a))C₁-C₆alkyl, C₁-C₆alkylcarbonyl, aryl, heteroraryl, aryloxy or heteroraryloxy, in whichthe alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy,aryl and heteroaryl groups may be optionally substituted with 1 to 5substituents independently selected from halogen, C₁-C₆ alkyl, C₁-C₆alkoxy, cyano and C₁-C₆ alkylthio; n is 0, 1, 2, 3 or 4; R₆ is hydrogen,halogen, C₁-C₆ alkyl or C₁-C₆ alkoxy; each R₇ independently representshydroxyl, mercapto, cyano, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkenyl, C₃-C₆ haloalkynyl, C₁-C₆alkylthio, C₁-C₆ haloalkoxy, C₁-C₆ haloalkylthio, C₁-C₆ alkoxycarbonyl,C₁-C₆ alkylcarbonyl, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆ alkenyloxy orC₃-C₆ alkynyloxy; m is 0, 1, 2, 3 or 4; or Two adjacent R₇ substitutentstogether with the carbon atoms to which they are attached represent aC₅-C₇ cycloalkyl (which may be optionally substituted with 1 to 3substituents independently selected from the group consisting ofhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio, and,additionally, a ring carbon unit may be replaced by an oxygen or sulphuratom); R_(a) is selected from hydrogen, C₁-C₆ alkyl, C₃-C₇ cycloalkyl,C₃-C₆ alkenyl and C₃-C₆ alkynyl, in which the alkyl, cycloalkyl, alkenyland alkynyl groups may be optionally substituted with 1 to 3substituents independently selected from halogen, C₁-C₆ alkoxy and C₁-C₆alkylthio; R_(b) and R_(c) are each independently selected fromhydrogen, halogen, cyano, C₁-C₆ alkyl, C₃-C₇ cycloalkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio, in which the alkyl,cycloalkyl, alkenyl and alkynyl groups may be optionally substitutedwith 1 to 3 substituents independently selected from halogen, C₁-C₆alkoxy and C₁-C₆ alkylthio; or a salt or N-oxide thereof.
 2. A compoundaccording to claim 1 wherein R₁ and R₂ are each independently selectedfrom hydrogen, C₁-C₆ alkyl and C₃-C₇ cycloalkyl, in which the alkyl andcycloalkyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio;or R₁ and R₂ together with the carbon atom to which they are attachedrepresent a C₃-C₆ cycloalkyl group (which may be optionally substitutedwith 1 to 3 substituents independently selected from the groupconsisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio);or R₂ and R₃ together with the carbon atoms to which they are attachedrepresent a C₅-C₇ cycloalkyl (which may be optionally substituted with 1to 3 substituents independently selected from the group consisting ofhalogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ alkylthio, and,additionally, a ring carbon unit may be replaced by an oxygen or sulphuratom).
 3. A compound according to claim 1 wherein R₃ and R₄ are eachindependently selected from hydrogen, halogen, hydroxyl, C₁-C₆ alkyl,C₁-C₆ alkoxy and C₃-C₇ cycloalkyl, in which the alkyl, alkoxy andcycloalkyl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₆ alkoxy and C₁-C₆ alkylthio;or R₃ and R₄ together with the carbon atom to which they are attachedrepresent C═O, C═NOR_(a), C═C(R_(b))(R_(c)) or C₃-C₆ cycloalkyl (whichmay be optionally substituted with 1 to 3 substituents independentlyselected from the group consisting of a halogen, C₁-C₆ alkyl, C₁-C₆alkoxy and C₁-C₆ alkylthio); or R₂ and R₃ together with the carbon atomsto which they are attached represent a C₅-C₇ cycloalkyl (which may beoptionally substituted with 1 to 3 substituents independently selectedfrom the group consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy andC₁-C₆ alkylthio, and, additionally, a ring carbon unit may be replacedby an oxygen or sulphur atom).
 4. A compound according to claim 1wherein each R₅ independently represents halogen, cyano, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy, C₃-C₆alkenyloxy, C₃-C₆ alkynyloxy, C₁-C₆ alkylthio, —C(═NOR_(a))C₁-C₆alkyl,phenyl, heteroraryl (wherein heteroaryl is pyridyl, thiophenyl,thiazolyl, imidazolyl or oxazolyl), phenoxy or heteroraryloxy (whereinheteroaryl is pyridyl, thiophenyl, thiazolyl, imidazolyl or oxazolyl),in which the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy,alkynyloxy, phenyl and heteroaryl groups may be optionally substitutedwith 1 to 5 substituents independently selected from halogen, C₁-C₆alkyl, C₁-C₆ alkoxy, cyano and C₁-C₆ alkylthio; n is 0, 1, 2, 3 or
 4. 5.A compound according to claim 1 wherein R₆ is hydrogen, halogen or C₁-C₆alkyl.
 6. A compound according to claim 1 wherein each R₇ independentlyrepresents cyano, halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₂-C₆ haloalkenyl, C₃-C₆ haloalkynyl, C₁-C₆ alkylthio,C₁-C₆ haloalkoxy, C₁-C₆ haloalkylthio, C₃-C₇ cycloalkyl, C₁-C₆ alkoxy,C₃-C₆ alkenyloxy or C₃-C₆ alkynyloxy; m is 0, 1, 2, 3 or 4; or Twoadjacent R₇ substituents together with the carbon atoms to which theyare attached represent a C₅-C₇ cycloalkyl group (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆alkylthio, and, additionally, a ring carbon unit may be replaced by anoxygen or sulphur atom).
 7. A compound according to claim 1 wherein R₁and R₂ are each independently selected from hydrogen and C₁-C₄ alkyl, inwhich the alkyl group may be optionally substituted with 1 to 3substituents independently selected from halogen, C₁-C₃ alkoxy and C₁-C₃alkylthio; or R₁ and R₂ together with the carbon atom to which they areattached represent a C₃-C₆ cycloalkyl group (which may be optionallysubstituted with 1 to 3 substituents independently selected from thegroup consisting of halogen, C₁-C₃ alkyl, C₁-C₃ alkoxy and C₁-C₃alkylthio).
 8. A compound according to claim 1 wherein R₃ and R₄ areeach independently selected from hydrogen, halogen, C₁-C₄ alkyl andC₃-C₄ cycloalkyl, in which the alkyl and cycloalkyl groups may beoptionally substituted with 1 to 3 substituents independently selectedfrom halogen, C₁-C₃ alkoxy and C₁-C₃ alkylthio; or R₃ and R₄ togetherwith the carbon atom to which they are attached represent C═O,C═NOR_(a), or C₃-C₆ cycloalkyl (which may be optionally substituted with1 to 3 substituents independently selected from the group consisting ofa halogen, C₁-C₃ alkyl, C₁-C₃ alkoxy and C₁-C₃ alkylthio).
 9. A compoundaccording to claim 1 wherein each R₅ independently represents halogen,cyano, C₁-C₄ alkyl, C₃-C₄ cycloalkyl, C₁-C₃ alkoxy, C₃-C₆ alkenyloxy,C₃-C₆ alkynyloxy, C₁-C₃ alkylthio, —C(═NOR_(a))C₁-C₆alkyl, phenyl,heteroraryl (wherein heteroaryl is pyridyl, thiazolyl or oxazolyl), inwhich the alkyl, cycloalkyl, alkoxy, alkenyloxy, alkynyloxy, phenyl andheteroaryl groups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, C₁-C₃ alkyl and C₁-C₃ alkoxy; n is0, 1 or
 2. 10. A compound according to claim 1 wherein R₆ is hydrogen orC₁-C₃ alkyl.
 11. A compound according to claim 1 wherein R₁ and R₂ areeach independently selected from hydrogen and C₁-C₄ alkyl, in which thealkyl group may be optionally substituted with 1 to 3 substituentsindependently selected from halogen, methoxy and methylthio; or R₁ andR₂ together with the carbon atom to which they are attached represent aC₃-C₄ cycloalkyl group (which may be optionally substituted with 1 to 3substituents independently selected from the group consisting of halogenand C₁-C₃ alkyl); R₃ and R₄ are each independently selected fromhydrogen, halogen and C₁-C₄ alkyl, in which the alkyl group may beoptionally substituted with 1 to 3 substituents independently selectedfrom halogen, methoxy and methylthio; or R₃ and R₄ together with thecarbon atom to which they are attached represent C═O, C═NOR_(a) or C₃-C₄cycloalkyl (which may be optionally substituted with 1 to 3 substituentsindependently selected from the group consisting of a halogen and C₁-C₃alkyl); each R₅ independently represents halogen, cyano, C₁-C₄ alkyl,C₃-C₄ cycloalkyl or phenyl, in which the alkyl, cycloalkyl and phenylgroups may be optionally substituted with 1 to 3 substituentsindependently selected from halogen or C₁-C₃ alkyl; n is 0, 1 or 2; R₆is hydrogen or methyl; each R₇ independently represents cyano, halogen,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₃ alkynyl, C₁-C₄ alkylthio or C₃-C₄cycloalkyl; m is 0, 1 or 2; and R_(a) is selected from hydrogen andC₁-C₄ alkyl, in which the alkyl group may be optionally substituted with1 to 3 halogen atoms; or a salt or N-oxide thereof.
 12. A compoundaccording to claim 1 wherein R₁ and R₂ are each independently selectedfrom hydrogen and C₁-C₃ alkyl; or R₁ and R₂ together with the carbonatom to which they are attached represent a C₃-C₄ cycloalkyl group; R₃and R₄ are each independently selected from hydrogen, fluoro or C₁-C₃alkyl; or R₃ and R₄ together with the carbon atom to which they areattached represent C═O or C₃-C₄ cycloalkyl; each R₅ independentlyrepresents halogen, C₁-C₃ alkyl or C₃-C₄ cycloalkyl, in which the alkyland cycloalkyl groups may be optionally substituted with 1 to 3 fluoroatoms; n is 0, 1 or 2; R₆ is hydrogen; and each R₇ independentlyrepresents fluoro, chloro or C₁-C₃ alkyl; m is 1 or 2; or a salt orN-oxide thereof.
 13. A composition comprising a fungicidally effectiveamount of a compound of formula (I) as defined in claim 1 and at leastone additional active ingredient and/or a diluent.
 14. A method ofcombating or controlling phytopathogenic microorganisms which comprisesapplying to a phytopathogen, to the locus of a phytopathogen, or to aplant susceptible to attack by a phytopathogen, or to propagationmaterial thereof, a fungicidally effective amount of a compound offormula (I) as defined in claim 1.